Jimmy Gets a Mouthful

For Barbie, last night had been the last straw.
The day previous, I had accidentally knocked over an expensive vase and had been spanked for it. That had been bad enough, but when I had thrown a temper tantrum in front of her friends last night, she was livid with me.
The night had started out badly when she had served me my all time least favorite food, creamed lima beans. Because I had resisted her efforts to feed me, much of it had ended up all over my face and bib. And then, when she had sent me to bed early at 6:30, instead of my usual 7:00, I had burst out in indignation. Of course, the condescending remarks made by her hot looking friends hadn’t helped the situation either.
Her first instinct to react to my outburst would have been another blistering spanking with the paddle but one of her friends had interceeded with an alternative. Not because she was opposed to seeing me get spanked, but because she had better ideas. I had watched as they huddled together and whispered conspiratorily amongst each other, hatching plans for my ultimate humiliation.
Needless to say, I was still sent to bed early, but I was warned that I would be punished tomorrow instead.
That night, I tossed and turned in my crib, the various possibilities going through my mind. If she were to tell Vanessa, I might get spanked twice, which would be terrifying to consider. There were any number of other punishments that Barbie could devise, of course. She had an inventive mind and she was always thinking of new and different ways to humiliate me.
This evening, Barbie announced that she was extending my bedtime, far later than I thought she ever would. It was when I would normally be getting ready for bed that she showed me that she had other plans in store for me.
Instead of getting a frilly nighty or onesie for me to wear for my long night in the crib, she instead picked out a very feminine gingham style dress with a pink and white checker pattern. It had big rows of frilly white ruffles around the bib style neckline and more along the short hem. I cringed as she lowered it over my head and I noted that it left my fat, bulging diapers clearly visible.
By evening, I had wet myself thoroughly and after taking my diapers off, Barbie instructed me to ”assume the position” over the crib. This meant that I was to lie over the crib mattress, face down, with my knees on the floor and grasp the far rails on the side of the crib. This was the position that Melissa had me take whenever she came over to do me from behind with her strap-on.
In this case, I was made to remain in position while Barbie stuffed a big fat buttplug into my protesting hole. I squirmed and whimpered but nevertheless, she succeeded in pushing the unwelcome object inside.
A sharp smack delivered to my rump told me it was time to get up and position myself on the changing table.
It had been a week since they had last milked me and I was predictably very horny. Barbie was wearing a low white lace top with a scoop neck and it displayed her deep cleavage and beautiful bosom in the most mouth watering way. Everytime I gazed down her top, my little pecker strained against its penis prison, the chastity device they kept me in perpetually, making me painfully aware of its presence.
She proceeded to diaper me as usual, with my triple thick cloth diapers and pink plastic panties and I feared a long uncomfortable night wearing the big buttplug.
However, Barbie dispelled that idea by putting knee socks and pink mary janes on me, obviously to take me out. Next, she put two floppy pink satin bows in my pigtails and applied a light makeup to my face which included a light blusher and pink glossy lipstick. When she was done, she put both items in my sissy purse and announced we were ready to go.
“Where are going?” I asked uncertainly as I clutched my purse nervously.
“To a strip club,” she said, much to my surprise.
She effectively terminated any further conversation by stuffing my cock shaped pacifier in my mouth. It made me feel partucularly sissyish to be stuffed from both ends, my back hole with a big buttplug and my mouth filled with cock.
We went outside where Melissa was waiting in her car.
After buckling me in the backseat, Barbie sat up front and she completely ignored me as she talked with her busty friend. I squirmed uncomfortably in the back as I felt the buttplug filling me up and stretching my hole unmercifully.
Fifteen minutes later, we pulled up next to Chippendales, a male strip club not far from Vanessa’s house. I was filled with dread by whatever they had in mind for me and they wasted no time rushing me into the backstage door. I could hear booming music outside and when we got inside, it was louder still.
I was led to a private room and my sexy companions closed the door behind them.
“Alright Sissy,” Barbie said as she looked at me severely with her steely green eyes, ”let’s get something straight. You are in some serious trouble and you’re looking at getting at least two spankings, on top of some of other things I can think of.”
I gulped in fear as my mind considered all the awful possibilities.
“You’ve been acting up lately and I think it’s time we brought you down a few pegs,” she continued.
“Now. You can either take your punishment, or…” her voice trailed off leaving me quaking with anxiety.
“Or-or what, Miss Barbie?” I asked shakily.
“Or…you can suck a little cock,” she said with a wicked smile.
My mouth dropped open in shock.
“You better think quick, Sissy. ‘Cause I’ve got your paddle right here and we can get started right now,” she said as she produced the familiar instrument of my punishment.
I looked fearfully at the polished wooden paddle, and I could easily imagine it harshly slapping my soft, tender bottom and making me cry. I felt hot tears brimming in my eyes and I thought anything was better than that option.
“I don’t wanna get a spanking,” I wailed imperiously.
“That’s about what I thought,” she said derisively and she began lowering my plastic pants down my shaven legs. I whimpered in fear since it appeared I was going to get punished no matter what. She unpinned my damp diapers and put them in a plastic sack that she’d brought with her in my diaper bag. From there, she produced a pair of silky pink panties, sheer in front and back and adorned with soft white ruffles around the leg openings. But what caught my eye was the extra hole between the legs and behind the crotch.
“These are called ‘back door panties’,” she explained as she snaked them up my legs and over my frightened bottom, “and you’ll soon see why.”
The two of them giggled at that and she bent over and pulled my buttplug out with a loud, embarassing pop.
“Looks like you’d better get down on your knees, Sissy-boy,” she said evenly.
As I sunk to my knees, she issued further instructions to me.
“When my friend comes in here, you are to ask him politely if you can suck him off, do you understand?”
“Yes, Ma’am,” I mumbled.
“And you are to address him as ‘sir’, got it?”
“Yes Ma’am,” I replied submissively.
Just then, a big man entered the room and after greeting both Melissa and Barbie, he immediately went over to the latter and gave her a great big bear hug. He dwarfed her in size and I gulped hard as he towered over me.
The big brawny dancer was dressed as a fireman and with his chiseled good looks, I could see his obvious appeal. His bare chest was like a barrel and he must have been six foot five and 250 pounds, easy. When he turned his attention to me, I froze in fear.
“So…this is the little panty-waist you were telling me about,” he said in a gruff, booming voice.
“That’s right, Honey,” she said as she reached up and ran her fingers through the hair on his chest, ”and he has something he wants to say to you.”
Everyone’s eyes turned to me and I took a deep breath and swallowed hard.
“Um…I um…I was wondering, um…can I…um…do you think I could, uh, kind of…er, suck you off?” I stammered nervously, my voice practically a whisper.
Barbie nudged me in the back with her knee.
“Please, Sir?” I asked timidly, ”may I please, suck your cock?”
He looked down at me with a strange look and he began slowly unshouldering his suspenders off his massive shoulders. I quickly saw that he was not wearing any underwear underneath and when his cock came into view, my mouth dropped open again in amazement. It was truly colossal, even limp, although that was quickly changing. Before my eyes, the monster began to grow and it quickly took on epic proportions.
I had never seen something so big in my life and as he stroked it, it rose up before my face like a a huge crane. The head was like a big blunt mushroom, about the diameter of a half dollar with veins coursing down his incredible shaft.
“P-please, please don’t cum in my mouth,” I begged him as my voice cracked.
He chuckled throatily and put his big heavy hand on the top of my head.
“Time to suck some cock, Sissy,” he said in a husky voice filled with desire.
“Wait,” I whimpered shakily, unsure of what I was getting into, ”I’ve never…I mean, I just-”
He cut off my hesitant protest by shoving his gargantuan member past my pink lipstick covered lips.
“MMMPHHH!!!” I squealed as he crammed it into my mouth.
I had to stretch my jaws as wide as they’d go to accomodate him and with his big hand on the back of my head, he forced his monster cock as far into my mouth as it would go.
“MMMMRPHHH!!!” I squealed again and I flailed my hands in the air in frantic circles, helpless to stop the raping of my mouth.
He laughed heartily and pulled it out briefly, before plunging it back in as far as it would go.
My pink purse gyrated around the crook in my arm until I steadied myself against his great, muscular thighs.
As he established a rhythm in my mouth, I noticed a ring of my pink lipstick encircling his thick shaft which showed the furthest depth of his penetration. I struggled to breath through my nose, even as my tongue was forced to savor the gigantic fleshy member filling my mouth. My cheeks stretched wide as he thrust it in and out and as I looked out of the corner of my eye, I saw Barbie taking pictures of me with a camera.
The taste of his manhood brought saliva to my mouth and I slobbered like a baby, the drool running down my chin.
“Looks like we need to get your little cocksucker his bib,” Melissa observed causticly.
Barbie giggled as she waited until the man had driven his big pole in as far as it would go, choking me with it, before snapping another picture. I blushed a deep shade of red at my compromising position.
Above me, I heard the man’s breathing deepen and his thrusts became more urgent. I gagged every time he jammed his cock into the back of my mouth and already, my jaw was beginning to grow sore.
My tongue sensed a change in the meaty phallus I was licking when all of a sudden, he crammed it as far in as it would go. With a loud roar that filled the room, the man came in my mouth, quickly filling it to overflowing with hot, salty cum. I sqealed in distress as he firmly held my head in place and pumped load after load into my mouth. I was forced to swallow the creamy goo and then swallow again as my mouth kept being refilled. I choked and gasped for breath and he pulled it out slightly but even as he did, more cum shot out of his cock!
I wouldn’t have believed it was possible!
The man continued to moan and I felt like I was chug-a-lugging from a firehose as his cum shot into my waiting mouth. After what seemed an eternity, it finally slowed to a dribble.
I sucked obediently on his massive head as the last bits of cum dribbled onto my tongue. As he pulled it out of my mouth, he held it before my face, still fully erect.
“Kiss it, Sissy,” he said breathlessly.
I gave the huge, wet head a tender kiss and he rewarding me by pushing it once more past my lips. I squealed in shock and he laughed loudly before pulling it back out.
Just as I was licking my lips and trying to catch my breath, I turned to see another hard-on staring me in the face. As my jaw dropped open, I looked up to see another Chippendales dancer grinning down at me. His crotch was shaven clean and without asking, he plunged his cock into my open mouth. I tried to scream but my mouth was filled with his manhood and I gagged once again. He immediately began pumping my mouth as he took hold of my head, using my pigtails as handles.
I whimpered and squealed even as I wrapped my lips around the man’s impressive cock. He responded by coaching my method, telling me to use more tongue, less pressure, take it in deeper, etc. In and out of my mouth, his big, slippery cock slid. My tongue caressed the hot underside of his member and I could feel him growing even harder in my mouth. He hammered the back of my throat and my head grew dizzy as he jerked my head back and forth to meet his thrusts.
Suddenly, with a loud bark of release, he exploded in my mouth, filling it with his creamy love juice. I swallowed a big load which was quickly replaced with another. He pushed his cock deep into the back of my mouth and held my head firmly with his hands to make sure I swallowed every drop like a good sissy. I did my best and I kept gobbling on cum until the man began to relax.
By now, other dancers had come into the room and all of them were avidly watching the spectacle of a sissy in a frilly gingham dress giving blowjobs.
As I lifted my head off of the cock in my mouth, I made sure to lick it clean of all the cum and slobber. That’s when I felt one of my pigtails being pulled forward and I saw a partially dressed dancer sitting on the nearby couch with his legs spread and his dick hard, obviously wanting more of the same.
I sighed and crawled over to him, lowering my mouth over his magnificent pole. I slurped and sucked, bobbing my head up and down dutifully as I made love to his cock with my lips and tongue. He moaned with pleasure and guided my head to a rhythm of his own choosing.
It was while I was distracted with him that I suddenly felt my back hole being lubed up with another man’s big finger. I squealed with distress as he plunged his middle finger in and pronounced me ready for another comer.
As I was still bent over with head in the first man’s lap, I struggled to get up. There was no way I was going to let another man hump me from behind!
I flailed my purse and tried to lift my head away but the first man easily held me in place. I felt the ruffled hem of my dress being pushed up exposing my bashful bottom to the entire room.
“OOOOMPHHH!!!” I screamed desperately, but to no avail.
I felt a hard, painful slap on my rump from the man behind me and then my cheeks being forcefully pried apart.
Melissa giggled and she came closer to get a better look, bending over so I could see down the front of her top.
“Now you’re going to really get it,” she assured me wickedly, “this is what all sissies deserve.”
As if to confirm her words, I felt a warm but blunt object pressing urgently against my back hole. So that was why they had put me in the panties with the extra opening!
I tried to squirm away from the insistent prodding the man was giving me but he held me with hands of steel. I also tried to protest but with my mouth filled with big meaty cock, everything came out muffled and indistiguishable.
Although I couldn’t see the size of the dick behind me, I could tell by the difficulty the man was having that it must have been titanic in size. As he pushed and poked, he’d slap my butt cheek in frustration, trying to will his impossibly big member into my hole. Finally, with a long, determined push, his head eased past my defeated sphincter, entering my forbidden back tunnel.
I moaned loudly around the cock in my mouth and the man only drove it deeper into my throat, throttling me with it. At the same time, the man in back plunged his pole deep into my rectum and I felt like I was being split in two. My eyes were as wide as saucers as he began slowly pumping me, grasping my frail hips and grinding his cock in as far as it would go. There was no doubt I was being made to endure the full sissy experience.
Somehow, with my back hole being stretched to capacity and my mouth being filled with another cock, I felt the distinct stirrings of femininity within me. I slurped hungrily on the juicy dick in my mouth, rolling my tongue around his shaft and swirling it in a loving caress. The man moaned in ectasy and I felt him begin to tense up. With my free hand, I cupped his balls, stroking them tenderly until he couldn’t take any more.
With a cry of joy, he blasted his load into my mouth, filling it with his creamy seed. I swallowed eagerly and then sucked again, getting a second and then a third helping as he emptied his orgasm into my mouth. For the first time in my life, I felt entirely fulfilled and I cleaned his cock lovingly with my tongue.
As the man behind me continued to drill into my backside, another man sat down to take the place of the one I had just sucked off. I kissed the head of his cock and then I felt Barbie’s hand pull my face away to face her. Quickly, she applied several wet coats of bubble gum pink lipstick to my lips before releasing me for my duty. I plunged my head down and over the man’s cock and he sighed with relief. Soon, I was bobbing up and down again while he guided me with his hand. Already, I was learning the best way to use my tongue and I could hear from his breathing that he was enjoying my efforts.
At the same time, my rear end was getting pounded mercilessly by the man behind me and he was making it harder for me to concentrate on the cock filling my mouth. My hole was sore from being stretched so wide and the guy hammered me with increasing intensity.
At last, he rammed it in as far as it would go and held it there, gripping my hips and squeezing hard. He came with a ear splitting orgasm, filling my canal with a warm, creamy enema. My own little weiner wanted desperately to respond but it was prevented from doing so by my chastity device. It strained miserably against the binding straps as the man behind me ground his gargantuan tool deep into my backside.
While the pain of my own unrequitted orgasm made itself felt, the man sitting before me happily blew his load into my mouth, filling it with warm, salty goo and I obediently swallowed again and again.
Slowly, both men pulled out of me and I stayed there, on my hands and knees, panting from the exertion. Everyone clapped and cheered for me and I blushed with embarrassment.
Barbie came over and peeled my clinging sheer panties down from my bottom and off my legs. Melissa had a fresh set of diapers waiting and everyone watched as I was put back into my normal underwear. One of the guys bent over and wiped a spot of cum off my chin with my pacifier before stuffing it into my mouth. While I savored the creamy flavor on my tongue, Barbie snaked my pink plastic panties up and over my fat diapers, completing my usual look. I could also feel cum dribbling out of my hole and for once, I was glad I was safe and secure back in my diapers, where I belonged.
It was then that I realized, more clearly than ever before, what I had been denying to myself all my life. And that was, that deep down, I really was just a big sissy, who desperately needed his diapers and dresses and all that comes with being one. Humiliation was something I’d just have to get used to and endure it as best as I could, just as I had, all my life. And if that meant that sometimes I’d have to suck some cock, or take one from behind, it was all for my own good. Other men, real men, would be the ones to enjoy women like Barbie, Melissa and Vanessa while I would have to be content with being milked every week and living a chaste life in my diapers and plastic panties. I realized that was the price I would have to pay for being a such a weak, effeminate sissy and I sighed at the epiphany.
Barbie took my hand and I swished out of the room, waving bye-bye to my new friends. I knew I would be back soon, to satisfy their needs in whatever way they required, Barbie would see to that.
For now, I would be sent to bed in my crib, with the taste of semen still fresh in my mouth.
Ah, the life of a sissy!

The End

Jimmy’s Potty Training Fiasco

I sat sullenly in the passenger seat of my mom’s car, as we made our way across town. Her words of scolding were still ringing in my ears from this morning’s diaper change.
“It’s time you started growing up, Jimmy,” she had said with obvious annoyance as she was pulling my peach colored plastic panties up my legs, ”I’m not going to keep changing your diapers forever, you know.”
It was that conversation that had prompted her to begin potty training me in earnest and she informed me of her intention that it was time that we went shopping for some training pants today.
That decision was certainly good news to me. Ever since we had moved away from the town where I had suffered endless humiliations and torments at Melissa’s hand, I had wanted to make a new start. Unfortunately, I hadn’t been able to get my incontinence under control and I was still wetting my diapers regularly, even during the daytime. Most of the time, there would be almost no prior indication that I had to go and sometimes I didn’t even realize what was happening until I felt the warm wetness soaking into the front of my diapers. Often I was unable to stop the flow until it was pretty much too late. By that time, there didn’t seem to be too much point in holding back any further and I’d just relax and let nature take over. My mom said that I just wasn’t trying hard enough and she had threatened me plenty of times with the paddle but I continued to insist that it wasn’t my fault.
Nonetheless, summer was quickly coming to an end and I was mortified at the thought of starting at a new school wearing the babyish undergarments. It was made worse by the fact that the diapers I wore were so thick and fluffy that I was unable to wear any normal pants over them. The exception were a pair of pink shorts I had inherited from the nurse at my old school but in reality, they were hardly any better than having my diapers fully exposed. They were snug fitting and with their white lace accents, they looked more like rhumba panties than gym shorts. However, it was either wear them or have my plastic pants visible to everyone.
So it was that today when we left the house, I was wearing a t-shirt, pink Ked’s sneakers, my triple thick diapers and my pink gym shorts. I have a rather slight, frail body, and my diapers billowed out prominently, making what I was wearing unmistakable, no matter what I was covering them with.
Of course, I was mortified to be seen in public like this. Only a blind man wouldn’t know that I was a boy in his mid-teens who still hadn’t graduated from wearing diapers. I absolutely dreaded having to go into a store or mall and I continually bit my lip with nervousness.
We stopped in front of a Long’s Drugs store and my mom shut off the car engine but I made no move to get out. My mom, when she reached the sidewalk and realized I was still in the car, gave me a frosty look of disapproval.
“Jimmy! You get your butt out of that car this instant!” she barked at me.
“But Mom!” I whined pleadingly.
“But nothing, Mister,” she snapped.
Coming over to my side of the car, my mom reached inside and grasped me by my ear, yanking me out of my seat.
“Owww!” I cried as I stumbled out after her, helpless against her hold.
A couple of young girls about thirteen witnessed my plight and giggled at me. When I stood up and bolted into the store, I heard them whispering with each other, no doubt about my obvious diapered condition.
My face was blushing fiercely as we entered the brightly lit store and I glanced around frantically to see who was staring at me. By some miracle, we were largely ignored as we headed through the aisles to the back of the store. I thought we’d stop at the adult diaper section since I was now fifteen years old but we kept going until we reached the pharmacist’s counter.
Behind the counter was a pretty brunette wearing a white uniform coat over her slim figure. Despite the long, shapeless form of her jacket, I saw immediately that underneath, she had a fantastic body, and her tight white top hugged her luscious bosom, revealing two youthful breasts like a ripe pair of cantelopes.
As we approached the low counter, I blushed anew as she gazed over at me with an amused look.
“Can I help you?” she asked my mom in a sweet, feminine voice.
“Yes. I’m looking for training panties for my Jimmy here. Do you think you have any in his size?” my mom asked matter-of-factly.
I coughed nervously as my face grew redder.
”Training pants, Mom,” I tried to correct her.
The young pharmacist lady smiled at me engagingly, showing her dimples as she looked down at my fat diapers.
“Mmm…I’m afraid not Ma’am, none that come that big.”
I blushed hotly and turned away to avoid her stare.
“Yes, it’s been hard enough trying to find diapers and plastic panties in his size,” my mom lamented.
The pretty woman giggled as she looked me up and down.
“Too bad Huggies doesn’t make any pull-ups in his size,” she mused as she tried to supress a giggle.
“I think I may have a place that you might try,” she offered, ”it’s called ABWorld, and it’s about a mile from here.”
My mom thanked her and got directions to the store before telling her goodbye. On our way out of the drugstore, we passed through the toddler’s section and my mom suddenly stopped abruptly.
“Now here’s what you need,” she exclaimed as she reached down and picked up a large potty chair made of sturdy pink plastic. On its side, in gaily written script amongst blocks and giraffes, were the words ‘Baby’s potty time!’.
I blushed as she handed it to me but I was grudgingly willing to pay that price to get out of my humiliating diapers once and for all.
We headed up to the front registers and I could feel everyone’s eyes on me, despite the gym shorts I was wearing over my diapers. I hated going out in public for this reason since there was no mistaking what I had on underneath. My bulky diapers stuck out blatantly and my bottom looked fat and rounded, all the more because of my skinny frame.
When we got up to the checkout counter, the middle aged lady took the potty seat from me to scan it but she stopped when she saw me fidgeting in front of her.
“Looks like someone’s about to start his potty training,” she announced, loud enough for everyone to hear. The checker behind us, an attractive woman in her late twenties, turned around and stared down at my thickly padded hips, before smiling broadly at me. I squirmed in embarassment as everyone within earshot stared openly at me.
”I’ll bet your mommy’s so proud of her little boy, now that he’s finally graduating from his pampers,” our checker said smiling down at me.
My face turned a bright red and I felt my ears burning with humiliation.
“It’s long overdue,” my mom answered as she paid for the potty seat.
“I’m sure it is,” the checker giggled as she handed my mom her change.
“Well, good luck with your potty training, Honey,” she told me as she handed the seat over to me.
I practically ran out of the store although the thickness of my diapers made it more of a brisk waddle. My mom followed me out and she gave me a look that showed her lack of sympathy for my situation.
After getting back into the car, we headed to the other store and found it without difficulty. Walking in, I was surprised to find the vast selection of items they stocked for adult babies. I had no idea such a place existed and mom went to find a salesperson.
A statuesque blond woman came over and greeted us warmly, looking me up and down appraisingly and I felt like she was undressing me with her eyes. She had an hourglass figure with an amazingly slim waist, made all the more impressive by the size of her big bust. She wore a loosely buttoned blouse of a light material over a low cut yellow halter top with a lacey, scoop cut. I tried not to stare at her deep cleavage but I found myself helplessly aroused by this tall, intimidating woman.
It had been a week since I had last masturbated and despite the intense humiliation I was feeling, I was ravenously horny. My mom was livid whenever I had been unlucky enough to be caught and such an event always resulted without fail in a blistering spanking, in addition to other punishments such as she saw fit.
She liked to subject me to random diaper checks, looking for any evidence that I had been playing with myself. Such evidence would bring about swift and painful punishment so I had to be exceedingly careful in relieving myself. The last time she’d caught me was about a half hour after she’d put me to bed, a time when I thought I’d be safe for my masturbatory misadventures since by morning, my diapers would be soaked with pee anyway, thereby hiding any trace of cum. However, on this surprise inspection, she’d caught me right after I’d shot my load of gooey semen into the snuggly soft folds of my diapers. The paddling that followed hurt so bad that I’d been forced to sleep on my stomach the rest of the night.
It was memories of that episode that were going through my mind as I gazed at the buxom amazon before us. Stimulated by such incredible sexuality, my little pecker was at full attention, although there was no visible indication of it, were anyone to look at the front of my shorts. My penis was so small and my diapers so thick that even with a raging hard-on, there was just no discernable bulge in front.
“How can I be of assistance?” the woman asked in a polite, yet firm voice.
I could easily imagine that she had a strong spanking arm.
“I’m looking for training panties for my son Jimmy here,” my mom began, ”do you have something for heavy wetter?”
I groaned inwardly. No matter how many times I corrected her, my mom insisted on calling my plastic and now training pants, panties.
“Oh yes! And congratulations!” she exclaimed to me enthusiastically, ”I’ll be happy to show you some panties that would be just perfect for your little boy.”
I really resented being referred to as a little boy but I didn’t want to cause a commotion that might result in a trip out to the car for a spanking so I remained silent.
“I’ll bet you’re very excited to begin your potty training, hmm?” she asked as she bent down to talk to me. She must’ve been over six feet tall because she towered over me, making me feel much like the little boy she was referring to.
In response, I mumbled under my breath and she led us to an aisle with cloth and disposable diapers.
“I would recommend these,” she said as she held before us a thick pair of cloth training pants. They looked soft but a lot thicker than I expected and they were decorated with a nursery print of baby rattles and playing bears. I didn’t like the fact that they were pink with white lacy borders and to me, they looked like they were intended for a little toddler girl, despite the fact that they were obviously in my size.
“These have an extra absorbent soaker pad sewn in between the legs for any ‘accidents’ he may have,” she explained informatively.
“I’m sure that’ll come in handy,” my mom replied sourly.
Suddenly, I felt the anger rising within me. These were little better than the diapers I was already wearing, maybe worse, since they were in such a babyish nursery print. I decided right then and there that there was no way I was going to let my mom get these for me. I was fifteen years old now and it was time for me to put my foot down!
“No!” I suddenly blurted out, with more vehemence than even I expected.
My mom, who was ignoring me as usual, turned to face me, a look of shock in her face. Even the sexy saleswoman gazed at me in surprise by my sudden outburst.
“What did you say?” my mom demanded.
The first inklings of doubt were already starting to creep into my subconcious as I wondered whether I was making the right move.
“No,” I repeated, now a little unsure, ”I don’t want to wear those. Those are for babies!”
I tried to sound firm and strong but my voice cracked and I came across sounding weak and petulant.
“You’re wearing baby diapers and plastic panties right now, Young Man,” my mom pointed out, her tone of voice taking on an edge, ”it’s a little late to be talking about looking like a baby.”
“No!” I repeated, crossing my arms in defiance, ”I won’t wear them!”
For a second, there was a brief moment of silence as the tension filled the air.
“Excuse me for a moment, we’ll be right back,” my mom told the saleswoman in a voice filled with determination.
The busty woman suppressed a giggle and nodded knowingly as my mom yanked me toward the door by my ear.
“I’ve had enough of your bad behavior,” my mom snarled at me under her breath, ”You’re going to get a little lesson in manners, Mister.”
My heart began beating wildly as I realized the horrible miscalculation I had made. Somehow, I had to placate her before it was too late.
She hauled me out roughly, never letting go of my ear and we passed another mother and her two young daughters on the sidewalk. We were parked right in front of the store and my mom only stopped by the side door long enough to reach in and retrieve the paddle. The sight of it filled me with dread and my facade of indignation evaporated like a drop of water in a fire.
“No Mommy! I promise I’ll be good!” I pleaded with her frantically.
The mother and her daughters stopped for a moment to see what was about to happen to this young man who was obviously still in diapers, and about to get them pulled down for a much deserved spanking.
My mom ignored my begging and proceeded to put down the tailgate of the SUV to provide herself with a seat and plenty of swinging room.
“No Mommy, please!” I wailed, ”I’ll wear those training pants now, please?!”
Tears were already brimming in my eyes as she sat down and yanked my pink shorts down roughly. I blushed as the young girls pointed at my thick diapers and began giggling loudly but I had little time to think about that. Within seconds, my mom had begun tugging my peach colored plastic pants off of my diaper and down my skinny thighs, leaving them just below my knees.
By now I was openly crying, partly out of shame, but also because I was trying to avoid the spanking I knew was coming in mere seconds. My mom jerked me over her lap angrily, unpinning my thick cloth diapers in a flash and exposing my small, bare round cheeks to the trio of onlookers.
Taking only long enough to push the soft, thick cotton layers back and between my legs, she placed her left hand on my back to hold me in place firmly while her other hand grasped the wooden paddle with grim determination. Up it swooped, before arcing back down to land in a loud, crisp ‘SMACKK!’ against my bottom.
I howled in pain and bucked on her lap as the paddle came down again and again, slapping my tender cheeks in its implacable mission of vengeance.
An endless stream of tears coursed down my face and my nose was running unchecked.
By now, the mother and her daughters had decided to watch the spectacle I was making of myself as I bawled like a baby. My legs were windmilling in the air as I struggled to maintain my balance while my mom spanked me with unrelenting vigor. Only when she had paddled my cheeks to a bright, candy apple red, did she stop and set the instrument of my punishment down.
I lay there, crushed with humiliation at this very public spanking and sobbed loudly, as my mom re-pinned my diapers over my stinging fanny. Several other shoppers, as they got out of their cars, had also stopped to watch and I knew my crying was only attracting further attention.
“Now,” she began, “You are going to march your little sissy bottom back in there and ask the nice saleslady if she will sell you those training panties. Do I make myself clear?” she demanded tersely.
“Y-yes, Mommy,” I whimpered between sobs.
Allowing me to stand up, my shoulders heaved as she brought my plastic panties back up my legs, tugging them roughly over my thick, bulging diapers. I thought she was going to do the same with my shorts but instead, she yanked them off from my ankles and threw them into the back of the car.
I cried out and tried to retrieve them but she slapped me sharply on the thick seat of my diapers.
“Those stay off for the rest of the day, Jimmy,” she said with finality and I sobbed miserably.
Now my diapers stuck out like a flashing neon sign and everyone who saw us, stopped whatever they were doing to stare at me.
Shuffling dejectedly back into the store, I caught sight of the mother who had watched my humiliating ordeal and now she was shaking her head as she looked me in the eye, no doubt disgusted by my lack of maturity. Her girls pointed at my shiny plastic pants and burst into giggles with no regard whatsoever to my pride. I blushed a bright shade of red that went all the way from my chest to my ears.
Walking determinedly, my mom pulled me alongside by my wrist while I waddled behind her, trying to keep up. My pathetic attempt to try and establish my authority had gone up in smoke and after the sound spanking, I was once again, docile and submissive as a lamb. What shred of willpower I had shown five minutes ago had been effectively and completely paddled out of my system.
We went back up to the tall, sexy saleslady, and I tried to wipe the tears off my face as she smiled down at me knowingly. Her expression clearly indicated that she knew exactly what had happened and I blushed furiously.
“Jimmy has something he’d like to say,” my mom announced formally.
With my bottom still blazing within my diapers, I was totally chastized and willing to submit.
“Um, uh, may I please, um, have those training panties, please?” I asked uncertainly.
“Well, you certainly may,” she said with an excess of politeness.
“And how many would you like, Sweety?” she asked as she reached over to the shelf to get them.
“Three pair, will be plenty,” my mom replied, ”I’m still doubtful that he has the maturity to be successfully potty trained, anyway.”
Tears of humiliation trickled down my face as the woman placed three of the childish panties in my hands. I stared down miserably at the colorful cartoon characters that covered the front and seat, realizing belatedly that my tantrum had achieved nothing except for a stinging spanking.

I sat on the potty seat fidgeting, still unable to make myself tinkle into the plastic container. I had been there for ten minutes straight and my mom’s patience was running out like water down a drain.
The thing was, she was making me nervous and my bladder was adamantly refusing to cooperate.
“Come on Jimmy, I haven’t got all day,” she reminded me for the second time.
We were in the bathroom and my new training panties were lying on the counter, alongside some plastic panties, waiting to be put on me for the first time. It was a momentous occasion for me, that I might actually be able to stop wearing my humiliating diapers but try as I might, my wee-wee was stubbornly refusing to help me out. My mom was tapping her feet impatiently, her arms crossed over her chest while she waited for me to “do my thing”. I was squatting awkwardly on the undersized (for me) potty seat, wearing my t-shirt but otherwise nude from the waist down except for my Ked’s sneakers.
Finally, my mom got tired of waiting. Yanking me up by my wrist, she smacked my still pink bottom and stood me up.
“All done? You’d better be, because I will NOT have you wetting your trainers like they’re diapers,” she lectured me. While she scolded me, she pulled the thick cloth training panties up my legs and into place. I looked down at the pretty pink panties, with their babyish nursery print of playful bears and rattles and I could feel my face redden. These were followed by a pair of clear plastic panties which she went on to explain;
“I’m going to be keeping an eye on you, Jimmy, ” she warned me in a serious tone, ”if I see a wet spot through these panties, there will be serious consequences.”
I gulped in fear and unconsciously rubbed my plastic covered bottom.
“Yes, Mommy,” I replied timidly.
“The bathroom is off limits to you. If you have to go potty, you call me, and I’ll pull down your trainers for you so you can use your potty seat. Do you understand me?”
“Yes, Mommy,” I answered.
After that, my afternoon progressed more or less normally. I fooled around with my legos for about an hour but when I stood up to get something off the counter, I noticed a small damp spot had appeared on the inside front of my plastic panties. I didn’t remember feeling an urge to go and it wasn’t much, but with the clear vinyl plastic, even a small spot stuck out prominently.
It made me nervous because my mom had been short tempered lately and this might be enough to trigger another painful spanking. While I pondered the situation, I suddenly felt a strong urge to pee come upon me. I was only just barely able to cut it off before I flooded my trainers so I knew I had to get to my mom fast.
Going into the dining room, I discovered that she was on the phone, deep in what appeared to be an important conversation. Standing before her, I tried to get her attention but she ignored me, waving me away like I were a fly that was annoying her.
Suddenly I felt another strong wave and before I could catch it, a little bit leaked out. I glanced down fearfully and with a sinking feeling, I could tell that it was now obvious that I’d wet myself. A light yellow stain the size of a silver dollar could plainly be seen where I had saturated one of the pink bears and one of the rattles. I bit my lip in angst and tried again to get my mom’s attention.
“Mommy! I gotta go pee!” I cried.
My mom gave me a frosty look and put her finger to her lips to silence me.
“….so what kind of interest rate can I expect on the long term bonds…” she continued to the person she was speaking with.
Suddenly, my dam broke. With an unstoppable flow, warm, wet pee flooded into my training panties, quickly drenching them and soaking them through. Although made of an absorbent cloth, these were not like my thick, thirsty diapers that could contain the quantity of wetting like I normally did. I gasped as a pool of unsaturated pee collected between my legs, threatening to leak out through the legs holes of my plastic panties. I let out a cry of despair as I looked down to see the puddle of yellow pee, easily visible through the clear vinyl panties, dribble past the elastic openings and down my inner thighs.
“Mommy!” I cried out instinctively, stamping my feet and bunching my fists in an urgent dance for attention.
My mom looked extremely irritated as she finally turned to me and saw what was going on.
“Look. I’ve got to go,” she told the person on the phone curtly, “I’ve got a situation I have to deal with here.”
I felt the seat of my trainers starting to soak up some of the excess pee as the flood finally slowed to a trickle. My mom made a quick impatient goodbye on the phone and then stood up to look down on me.
“Jimmy!? Do you know who that was I was talking to on the phone?” she demanded angrily.
“–It was a very important person,” she snapped, “and I don’t have time to deal with babies like you everytime you feel you want to tinkle!”
“But I–” I tried to stammer.
Without another word, my mom reached into her purse where my paddle waited, polished to a high shine from so much use. Grabbing me by my ear, she lifted me up until I was almost on my toes. The wooden paddle shrieked through the air, landing on my plastic pantied seat with a dull SPLATT!!
I cried out in fear and dismay and jumped with surprise. The sharp impact of the paddle caused more of the warm pee to escape and it dribbled down my inner thighs humiliatingly.
So angry was my mom that she hadn’t even waited to pull down my trainers or plastic panties. She swatted at my captive bottom again, sending my wet cheeks a message that said, this is just a taste of what you’ve got coming.
After the first two swings, my mom tore my plastic panties down to mid-thigh level, lashing out again. The paddle landed with a stinging splat and a squish and I felt even more childish that my sopping wet training pants were hugging my round, sissy bottom snugly. Even though the wet cloth was fairly thick, my mom had a seasoned swinging arm and her paddle made itself felt with a stinging bite, even through the training panties.
My bottom was already sore from my earlier spanking and these deep, fearsome swats quickly pushed me over the edge. I burst into tears even as she jerked my wet trainers down to join my plastic panties.
Now my wet bottom was bared and defenseless, dreading the impact of the harsh wooden paddle on its yeilding, tender surface. My mom didn’t hesitate and she slapped my pink cheeks soundly, smacking them singly, and then together. My soft, round cheeks jiggled each time the hard wooden paddle struck them and they blushed hot red with each punishing impact. I wailed and sobbed, dancing on my feet but I was unable to escape the terrific onslaught against my youthful bottom.
I cried like a baby, my tiny little pecker jerking up and down while I howled in pain.
For the second time today, my face was wet with tears as I bawled unashamedly. Everytime my torso swung forward, trying to escape the paddle, my mom would pull me up with her other hand and swat my blushing wet fanny with the other. The sting is always twice as bad on a freshly wet bottom and today was certainly no exception. My cheeks went from pink, to bright red, to a deep, flaming reddish crimson. She’d look for a spot that was only a shade less red than the others and then she’d let me have it twice as hard there. I was crying so hard I could only gasp for breath between my piteous sobs of sorrow.
At last, she stopped the painful spanking and let me catch my breath.
“Well Jimmy. I thought you were ready for training panties but evidently you’re not,” she scolded me.
She emphasized her point with another harsh slap to my unsuspecting bottom.
I bellowed out in pain and a fresh torrent of tears spilled down my wet cheeks.
“Since you can’t control yourself any better than a baby, I’m putting you straight back into your diapers for the rest of the day!”
I sobbed in shame as she set the paddle down with a clatter and led me to my bedroom where my diapering supplies were waiting. As she let go of me, I rolled onto the changing pad on my side, afraid to let my burning bottom make contact with the plastic vinyl of my changing table.
“I don’t know why this is so difficult for you,” she chided me as she pulled out a triple stack of cloth diapers and positioned them under my rump, “you’re nothing but a big baby–do you know that?”
I nodded my head between sobs, hoping to diffuse my mom’s angry mood.
“You can start your nap early today,” she said infuriatingly as she pulled the ends of the thick diapers together so she could pin them, “that way you can’t get into any more trouble than you already have.”
I sobbed again as the diapers rubbed against my blazing cheeks, only to have the inferno sealed up tight as each side got pinned securely into place. Shaking out a pair of white nursery print plastic panties, my mom tugged them up my legs and jerked them around the bulk of my diapers.
“Now, get into bed! I don’t want to hear so much as a peep out of you for the rest of the afternoon!” she said as she slapped my thickly diapered fanny.
With sunlight peeking through the curtains, I made my way into bed miserably, crying myself into a fitful sleep.

The next morning, after a very wet night in my diapers, my mom reluctantly announced that we would resume my potty training. I was much relieved and twice as determined to do a better job today than yesterday.
After breakfast, my mom removed my wet diapers and put me in a bubble bath to get me cleaned up. I would have preferred to be left alone to clean myself but my mom would have none of it. Instead, she leaned over me and washed me thoroughly with a soapy washcloth, making sure to she devoted extra attention to my private areas. It was humiliating to have my own mom washing me like this but there was little I could say about it.
After my bath, my mom continued with her ministrations, drying me off with a big fluffy towel, despite my protestations.
Taking me by the hand, she sat me down on my potty seat and told me brusquely to “do my business”.
For some reason, I just didn’t feel the need to go, and of course, her presence standing over me certainly didn’t help. It could be that I had just peed most of my morning urges into my diaper when I was at breakfast. Typically, I’d wake up with a strong urge to go and I’d simply pee into my already soaked diaper, either while I was still in bed, or later, at the breakfast table. Since my mom never changed me before we ate, it helped to warm up the wet, clinging cloth until I could get into a fresh pair.
“Jimmy,” my mom said evenly as she watched me on my potty chair, “I hope this isn’t going to be a repeat of yesterday.”
“But, Mommy, I don’t have to go right now,” I whined.
“Well you can just sit there, Young Man, I won’t have you wetting your training panties like they’re diapers–”
Just then, the doorbell rang and I froze in fear.
“Don’t you move an inch,” she warned me with a wag of her finger.
As she left the bathroom, I heard her steps as she walked out to the front door. Part of me wanted to get off my potty chair and sit on the toilet although there really wasn’t any point, since I didn’t have to go anyway.
Hopefully, the person at the door was the mailman or something and would soon go away.
I strained my ears to try and hear what was taking place.
It sounded like my mom recognized whoever it was, possibly a young woman, and I heard the door close.
OH NO! I heard two sets of steps coming toward the bathroom. What was I to do? Whoever was with her was soon going to be coming around the corner, where they’d see me squatting over my potty chair like a little toddler! I bit my knuckle in anxiety and panic just as they came through the door.
“And here’s my little troublemaker,” my mom said by way of introduction.
The young woman behind her was quite stunning in her short white shorts and yellow crop top. She looked to be only a couple years older than me, maybe seventeen or eighteen, with long dark hair and beautiful brown eyes. Her flat, firm tummy was exposed below the tight top that was stretched smooth around her two perfect breasts.
“Oh, he doesn’t look like too much trouble to me,” she said with a dismissive grin, no doubt influenced by my pathetic appearance.
I blushed hot red and looked away, my eyes brimming with tears of shame.
“I’ve just started Jimmy’s potty training, as you can see, although we got off to a bit of a rocky start yesterday,” my mom explained while the sexy brunette giggled with amusement.
“Like I said on the phone, normally, Jimmy wears thick diapers during the day but I’m hoping that he’s finally ready to grow up and move on to training panties.”
The tall girl knelt down and grasped me lightly by my chin, turning me to face her.
“Well, hello there, Jimmy,” she said very sweetly, “my name is Susan.”
Her voice sounded as if she were addressing a small child, rather than a fifteen year old guy.
My face was a bright red and I could feel the heat all the way up to my ears.
“Hi,” I croaked, keeping my eyes downcast. I could see that she had long, smooth legs and I was so humiliated to be seen like this, by such a sexy girl who was practically my peer.
“You won’t wet your training panties today, will you?” she said encouragingly.
I shook my head as I blushed an even deeper red, if that was possible.
“That’s good,” she said, “because if you do, I’ll have to put you back into your baby pampers, okay?”
I nodded my head but kept it down to hide my shame and tears.
“Susan is going to be your babysitter today while I’m gone,” my mom said authoritatively, “you are to do exactly as she tells you. Do you understand me Jimmy?”
“Yes, Mommy,” I mumbled.
“And if I hear you’ve been disobediant while I’m away, you’ll be taking another trip over my lap. Do I make myself clear?”
“Yes, Mommy,” I repeated.
Susan giggled as she looked down at me.
“I’m sure you’ll be a wonderful little boy for me today, won’t you Jimmy?” she said in her sweet voice.
I nodded in embarrassment, humiliated at being treated like such a infantile child.
“All done?” my mom asked, pointing at the potty chair, “I have to get going.”
I nodded and my mom unceremoniously stood me up. I frantically tried to cover up my miniscule weiner but it was too late. Susan was looking right at it and she broke into laughter before she could stifle it.
“I’m sorry,” she said as she covered her mouth with her hand, “it’s just so…tiny!”
I grimaced and looked away as my face burned with shame. My mom put my feet through the leg holes in the training panties and raised the childish underwear up and into place. She followed these with a pair of translucent pink plastic panties with white ruffles around the leg holes and waist. Even though these weren’t as see-thru as the clear ones I was wearing yesterday, the colorful nursery characters were still plainly visible and the soft white ruffles made it look twice as babyish.
“There,” she said as she slapped my pantied bottom, “Susan can finish dressing you. I’ve got to get going or I’ll be late.”
The two of them made their goodbyes and I was left alone with Susan who took me into my bedroom.
“Well, let’s see what we can find for you to wear today,” Susan said brightly.
“I can dress myself,” I said sullenly.
“Now let’s not have any of that,” she replied, her tone taking on a barely perceptable change, “Your mommy left your paddle for me to use if I need it.”
She picked up the wooden paddle and smacked it against the palm of her hand.
“I’ll bet that hurts on a little boy’s bare bottom, doesn’t it Jimmy?” she prompted me.
I blushed deeply at her humiliating question.
“I’m not a little boy!” I complained bitterly.
“Aww…well, you sure look like one in your trainers and plastic panties,” she teased me.
I bit my lip, unable to come up with a satisfactory response to that one. If I could only keep them dry for the afternoon, perhaps I could finally get back to wearing adult clothes again, I reasoned. I certainly didn’t want this sexy babe to see me wet myself, that was for sure.
As she went to my closet, she picked out a pair of jeans and a t-shirt for me to wear.
“Tell you what, Champ,” she offered, “how ’bout we go out and get some ice cream. Would you like that?”
Suddenly, things were starting to look up.
“Okay,” I said, somewhat warily.
If I was able to wear jeans over my trainers, and not have any other babyish clothing visible, I might be taken for any other teenager, instead of a bedwetting little sissy. Not to mention that I’d be in the company of this hot babe, and onlookers might actually mistake her for my girlfriend. Wouldn’t that be great!
I let her dress me in my normal clothes happily now, looking forward to being treated with respect and envy by those around me. The jeans were a bit snug but certainly far better than having to wear my fat diapers and a pink pair of tight shorts.
“How old are you Jimmy? Thirteen?” she asked as she lowered my t-shirt over my head.
My face reddened again at her underestimating assumption.
“I’m fifteen,” I told her.
“Oh. Sorry,” she said, although she didn’t sound sorry at all.
Taking my hand, she led me out to her car and we got in. It was only a short drive to an ice cream stand nearby our house and we arrived without incident. I had the opportunity to study her fabulous body on the way and I was horny and excited by the time we pulled up. She had long, curly hair, the color of dark chocolate, and it spilled over her shoulders and over her perky, big boobs. Normally I would never have the chance to be this close to such a knockout so I didn’t want to blow it by staring at her sexy cleavage, despite the irresistable temptation to do so.
We walked up to the ice cream stand and I picked out a cone for myself. There was no one else around and I relaxed, hoping the woman behind the counter might think Susan and I were going together. In any event, she didn’t look me up and down like I was used to so that was good enough for me.
I was licking from my cone when Susan’s cell phone started ringing from inside her car. Content to stand there in the sunshine and enjoy being outside, I stood and enjoyed the moment, since it was rare that I ever got out.
It was then that a pair of girls walked up behind me to order some ice cream for themselves. Hearing their young voices, I turned around and saw a pair of cheerleaders, presumably from the school nearby. They looked to be about sixteen or seventeen and totally hot. Their uniform was an extremely short pink mini-skirt which just barely covered their small, sexy buns and above that, they had on a tight, shimmery pink halter. Both were in outstanding shape, with slim waists and lithe arms. I held my breath as I gazed hungrily at their beautiful breasts, hardly contained by the thin, stretchy fabric of their tops and I felt my temperature inexorably rising as I admired these sweet foxes. My heart began beating eagerly when I saw just how pretty they were. I figured they must be two of the most popular hotties in school!
I was enraptured by their sexuality and as they walked off under the shaded awning, I admired their firm sexy legs and bouncy fannys. When they turned around and began talking with each other, they glanced over and saw me for the first time. Perhaps emboldened by my sexual frustration, I forced myself to smile weakly at them. They didn’t respond immediately and I felt myself blushing at my audacity. They were so hot I couldn’t believe it!
I watched them out of the corner of my eye as they spoke in hushed tones with each other while Susan was engaged on her cell phone in the car. From time to time I heard giggles from the two and when I glanced over, I noticed they were both looking at me. I saw they were smiling so I figured it couldn’t be too bad, could it? Maybe one of them liked me, I reflected. Wouldn’t that be something! This would be a memorable day indeed if I were able to make a girlfriend on my short trip outside. Especially one as hot as one of these two honeys. I had never had anything even remotely resembling a girlfriend so anything I could establish today would be a big step forward.
Things were really coming together for me, it seemed.
Suddenly, the bleach blonde haired one came over, followed immediately by her cute friend. I would have been delighted to have either one but I found the bold look on the blonde’s face strangely exciting. She had smooth, satiny skin and high cheekbones, giving her the look of a model. I tried to stand up straight and look nonchalant as the pair came over to me. I wished I could think of something clever to say but my mind was blank and my mouth, dry with anticipation. They were still smiling as they stood in front of me and they fixed me with that confident look worn by all women who know they are ravishingly beautiful. The blonde had very full, sensuous lips with pink lipstick and they formed a provacative, yet challenging smirk.
“Are you wearing diapers?” she suddenly asked bluntly.
I immediately turned a deep shade of red and my shoulders slumped in defeat as my mouth dropped open in shock.
” ‘Cause it looks like you are,” the other one pointed out with a sneer.
“No-I’m-not!” I replied indignantly, although the color of my face belied the truth.
“I think you are,” the blonde said as she put her hands on her curvy hips in a bold stance, “are you some kind of sissy or something?”
This wasn’t at all how I expected our conversation to go! My mouth opened and closed as I frantically sought a way to reverse my disasterous situation.
“I’m not a sissy!” I stated petulantly.
The two girls giggled as they exchanged looks but before I knew it, they were grabbing for the zipper on my pants. With one hand holding my ice cream, I was helpless to fend off four others and within seconds, they had unbuttoned the first button and unzipped my fly. My pants dropped to my ankles like a flag surrendering, in a humiliating display of sissy capitulation. My t-shirt was far too short to cover anything and now my trainers and shiny pink plastic panties were there for all to see.
The two babes burst into uncontrollable laughter, slapping their knees in a fit of mirth while I gasped in shock. When I tried to reach down and grab my pants, the blonde reacted quickly and she pushed me backwards, making me lose my balance. My ice cream cone went flying and I fell on my rear end with an embarassing thud. As they stood over me laughing, the trauma was just too much. To my horror, I felt the front of my trainers growing wet and warm as I proceeded to helplessly soak them.
My hands shot down to cover my babyish act which only served to bring further attention to it.
“Stop it!” I squealed, perilously close to tears.
“What a sissy!!” the cute brunette exclaimed, when she was able to stop laughing.
I finally regained control over my bladder but the damage was already done. The entire front of my training panties were completely saturated and it was totally obvious to everyone present, including the ice cream vendor.
“Oh my god! Did you just wet your diapers?!” the blonde asked incredulously.
“They’re not diapers!” I cried, “they’re trainers!”
I always seemed to say the stupidest things, especially when women were involved, and in this case, my remark sent them into another fit of laughter.
“Oh!” the blonde giggled, “Trainers!”
Just then, Susan walked up to see what all the commotion was all about.
“What’s going on, Jimmy? Did you have an accident?” she asked.
Finally I was able to grab my pants and yank them up, covering my shameful pink plastic panties from view.
“I wanna go home now,” I sniffled as I fought back the tears.
“Awww, and you lost your ice cream too,” she said trying to comfort me.
“You know this guy?” the brunette asked in surprise.
“Well, I’m his babysitter today,” Susan replied, apparently not overly concerned with the fact I had just been humiliated like never before.
“His Babysitter?” the blonde gaped.
Both broke into a fresh peals of laughter and even Susan had to suppress a smile.
“Yes, I’m afraid his mom’s trying to potty train him, although it doesn’t look like he’s doing too good with that.”
The girls shook their head in amazement that such things happened.
“Well, you’d better take him home to his mommy, it looks like he’s going to need to be put back into his diapers, from what I’ve seen,” the blonde derided me.
Susan sighed.
“I’m afraid so. Come on Jimmy, let’s take you home,” she said with resignation.
I was sniffling as I zipped up my pants and trudged back to the car in defeat.
I was so humiliated, I wanted to cry and it was only with great effort, that I was able to keep my composure.
“You didn’t do anything to save me!” I bitterly lashed out at Susan when she got into the car next to me.
She surprised me by turning to face me and then slapping me hard on the cheek.
“Now you look here, you big sissy! It’s about time you grew up and started acting your age! If you weren’t such a little baby, maybe people would treat you with a some respect,” she snapped at me.
I rubbed my stinging cheek as the tears rolled down my face, despite my best intentions. Now, even my beautiful babysitter thought of me as no better than a diaper dependant toddler.
“I couldn’t help it,” I whined piteously.
“All I know is that we’re headed straight home and then I’m going to put you right back into your diapers for your nap. I’ve never met such a sissy in my entire life,” she said disgustedly.
I sniffled and furiously wiped at my tears as I struggled to stop acting like a crybaby.
I knew my mom would be livid when she found out I’d wet my trainers again and that’s when the real fear started sinking in. I could easily see her angry face as she held the wet pants before me and scolded me with her harsh words. The next thing that would happen was that she’d haul me out of bed or wherever I was and yank my diapers down for a blistering spanking.
And my bottom was still tender from yesterday’s paddling.
I didn’t want to sound like a total wimp but I had to try and convince Susan to help me.
“Um…you aren’t going to, um, tell my mom about this…are you?” I asked timidly, like I was walking on thin ice.
“What do you mean–about wetting your pants? Of course! You obviously need diapers,” she replied curtly.
My heart sank. Already my bottom was tingling with the anticipation of another hard spanking.
“Well…don’t you think…just this once…you might, kinda…you know…forget about it?” I asked hopefully.
“I don’t think so, Jimmy. When your mommy gets home, she and I are going to have a nice little talk and then she can decide how she wants to discipline you,” she told me in a voice reserved for four year olds.
I sank down into my seat in despair as I saw my last possible avenue of mercy slam shut in my face.
When we got back home, Susan wasted no time in taking me to my room where she stripped me of my wet trainers and tossed them into the diaper pail. She wiped my bottom and crotch with baby wipes and then applied a thick coating of diaper rash ointment to my cheeks. I was devastated to have this pretty female putting me back into my diapers and I swallowed a sob of embarassment rising in my throat.
Wordlessly, she placed a waiting set of soft, thick diapers under my rump and pinned them into place expertly, as if she had been changing sissies all her life. When she saw me looking down her deep cleavage, she slapped me again and wagged her well manicured finger in my face.
“Don’t think for an instant that you’ll ever get to see those,” she said referring to her tremendous breasts, “those are for real men, not diaper wetting sissies like you.”
I pouted angrily as she stuffed my pacifier into my mouth and shook out a pair of pink nursery print snap-on plastic panties. These were the ones with cute bunnies and flowers on them and I was mortified at her choice of panties for me.
“Just look at you, Jimmy,” she told me as she slid the plastic panties up my legs and over my thick, bulging diapers, “fifteen years old and still wearing diapers and plastic panties like a little baby.”
She shook her head and her eyes bore into me with disapproval.
Going over to my closet, she fished around until she found a pink frilly nightey for me to wear and as she put it over me, I felt just like the immature baby she was calling me.
“You should be spending your naps in a proper crib like the big baby you are but I guess this bed will just have to do,” she said as she slapped my fat, diapered rump.
I climbed into bed and heard the crinkly sound of my waterproof sheets which faithfully and audibly announced that a bedwetter slept here.
Susan shut out the light but left the door open where she stood, her fabulous body framed by the light in the hallway.
“And I better not catch you masturbating, or it’ll only add to the spanking you’ll get when your mommy comes home,” she told me firmly.
Her words filled me with dread and trepidation. Now for sure I’d be getting paddled and I sucked on my pacifier desperately.
Today had gone so badly and it was still only noon!

After a long, restless nap, my mom finally came home and I listened nervously from my bed as she came in the house and I heard her greeting Susan. I lay perfectly still so that the noise from my waterproof mattress cover wouldn’t obscure the conversation that I was straining so hard to hear.
“Hello, Mrs. Turner,” I heard Susan say.
“Hi Susan, how did it go today?” she replied cautiously as she set down her keys.
“Not good, I’m afraid,” I heard my babysitter responding, “Jimmy had an accident and he soaked his training panties not even an hour after you changed him.”
I bit my lip anxiously, the whole humiliating scene re-living itself in my mind.
“Not again!?” my mom responded, her voice rising up in anger.
“Mm-hm, I put him immediately back into his diapers and he’s taking his nap right now,” she explained.
I didn’t hear anything from my mom and Susan went on.
“If you ask me, I really don’t think he’s ready for training panties yet, Mrs. Turner. Personally, I think he’s just too immature.”
I burned with angry resentment at her quick evaluation of me. It was so unfair!
I wanted to shout out that I could handle the same underwear that all my peers were wearing and that I didn’t need diapers and plastic pants, despite the fact that my loins were surrounded at present by the clammy wet cloth of my most recent wetting.
“Well that does it,” my mom announced firmly, “perhaps you’d like to remain for just a moment to see how I discipline little boys who wet their pants.”
“I’d love to!” she said gaily.
I hated her enthusiasm at being offered to be a witness at my punishment but my resentment had to take a back seat to the fear now building inside me. My stomach buzzed with nervous anticipation and I gulped anxiously as I sucked my thumb like a toddler. I could hear my mom’s angry footsteps coming down the hallway and I froze in terror of the inevitable spanking that would soon be administered to my waiting bottom.
A second later, my door opened the rest of the way and my mom walked through, closely followed by Susan.
“Jimmy! You’ve got a lot of explaining to do,” she barked as she picked up the paddle from the top of the dresser.
I bolted upright in bed and tried to hide behind the baby blankets I was holding protectively around me.
“I-I-I-” I stammered helplessly.
Susan looked at me without sympathy, in fact, she had a look of cool satisfaction on her pretty face that I found particularly frustrating. Her air of superiority was quite clear to see and my frustration was exceeded only by the waves of humiliation that were washing over me. Not only had she seen me wet myself, now she was going to be present while I got my bottom paddled.
“Stand up,” my mom ordered me tersely.
I began crying crocodile tears as I anticipated the blistering spanking I was about to receive and reluctantly I rose off of my bed to stand before my angry mother.
She immediately sat down on the bed and turned me around roughly to face Susan who was watching me with her arms crossed over her fantastic chest. Even in my heightened state of panic, I couldn’t help but notice the two soft mounds of her bosom, pushed up in a teasing display of sexuality denied to me.
My mom squeezed the seat of my thick diapers, checking to see if I was wet, a humiliating gesture that made me want to cry in front of this beautiful girl, all the more because of what she discovered.
“Wet again, I see!” she announced in exasperation.
I sniffled sadly and looked down at the ground, my lower lip trembling.
“I’m sorry Susan, but I’m afraid Jimmy’s going to get his bottom paddled for his misbehaviour,” she said although I knew she wasn’t sorry to have Susan see me get punished. “Jimmy, I want you to apologize to Susan for wetting your pants today,” she ordered me.
I sniffled and choked down a sob of embarrassment.
“I-I’m s-sorry…I-I wet my pants,” I muttered abjectly.
“Maybe this will teach a lesson, Jimmy,” she said, full of smug superiority.
A tear rolled down my cheek as my mom turned me back around to face her lap, the wooden paddle in her hands ready for use. Taking me over her knee, my mom ripped my plastic panties open with one downward yank, the snaps on both sides popping open easily. I felt the familiar sensation as she unpinned the thick, wet cotton cloth and pulled my diapers back, leaving my bare bottom pointing upward and ready to recieve the harsh slaps of the paddle.
Looking up at Susan, I saw a smile appear on her pretty face and I sobbed in despair.
When the paddle seared itself on my rump, I cried out like the baby everyone knew I was.

I woke up the next morning with my bottom still sore and tender, to the babyish sounds of my nursery rhyme alarm clock. My mom had bought it for me when I was in the first grade and she didn’t see any reason to get rid of it since it still worked fine. I hated it because the childish melody of “little teapot” sounded like something a mother would use to lull her baby to sleep in a crib and it seemed to serve as a daily reminder of my infantile behaviour.
I noticed I was hugging my teddy bear for comfort and still sucking on my pacifier. The latter was a habit I just couldn’t seem to kick and despite the fact that I knew it made me look like a baby, I couldn’t help myself. Sometimes, in the middle of the night, I’d lose track of the babyish accessory and I’d suck my thumb instead, much to my mom’s chagrin. She had gone as far as coating it with vinegar but it still happened from time to time that she’d wake me up and my thumb would be buried in my mouth while I sucked it like a baby. That’s when she’d wake me up with a sharp slap delivered to my bare thigh.
My mom came in and we began our usual morning routine. Breakfast, followed by my bubble bath, which today hurt when my bottom first made contact with the hot soapy water. When I cried out, my mom showed little sympathy saying, “maybe that will serve as a reminder that your training panties aren’t to be used as a toilet.”
After drying me off, she informed me that I still had one pair of trainers left that I hadn’t wet in and that this would be my last and only chance to redeem myself.
“Three strikes and you’re out,” she said as she snugged the sissyish panties up my bare legs, covering my tiny penis once more.
“I’ll do better today, Mommy,” I promised her, my voice filled with hope.
“You’d better,” she said skeptically, “otherwise you’ll be starting the new school year, back in your diapers and plastic panties.”
I shivered at the thought of that prospect. It was a situation that would surely end in further humiliation, just as it had at my last school.
My mom completed her dressing of me by pulling up my plastic panties, a pink pair like yesterday with soft white ruffles around the leg holes and waist. The only good thing to be said about these panties, which my mom had picked up a quantity of on sale, was that they were very comfortable to wear. They didn’t cut into my thighs but they were still surprisingly leak proof and the soft ruffles constantly caressed my upper legs as I walked about in them.
After she left me to do as I pleased, I felt I should take advantage of the slimmer underwear and go outside again, although I certainly wouldn’t be going anywhere near the ice cream stand we were at yesterday. I put on some more loose fitting jeans (I hadn’t been careful enough about that yesterday) and a t-shirt and asked my mom if I could go play outside and that I’d only be gone for a short while. She was hesitant to let me out of her sight unsupervised but after pleading with her, I somehow convinced her that I was old enough to go without her.
“You’ve got one hour exactly,” she said as she checked the time on her watch, “I want you back in plenty of time for your nap.”
“Yes, Mommy,” I replied happily.
I walked down the street carefully, trying to gauge the reaction of people who passed by me, to see if they noticed the thick underwear I had on underneath but so far, no one seemed to notice. It gave my shaken confidence enough of a bolster to risk going over to the nearby park. It was a nice day out and people were enjoying themselves on the grass, either playing ball or having picnics and I noticed there were many young people the same age as me to be seen.
I almost felt mischievious, that I was succeeding in concealing a great secret from the people around me and I stifled a chuckle of amusement as I walked through the wide, grassy park. I was feeling pretty good about things and not paying attention to where I was going when all of a sudden, I caught sight of a group of cheerleaders practicing their routines that I was in danger of stumbling into. I hadn’t noticed them before since I had been looking the other way, but now that I had, it was impossible for me to go unnoticed. In a flash, I recognized the super short pink mini-skirts and shimmery clinging tops of the same type the two girls were wearing yesterday and I froze in panic. I immediately turned around but my abrupt change in direction only drew attention to me and I hadn’t walked five feet when a girl’s voice called out to me in a strong voice.
“Hey!” she shouted, “Hey you!” and I knew with sinking certainty that it was the bleach blonde from yesterday.
I hesitated momentarily but with great effort, willed myself to ignore the demanding summons from behind me. This was especially difficult for me since all my life I had been taught to respond immediately whenever called upon by a woman. It was deeply ingrained and I had learned the price for such disobediance was frequently a sound spanking.
“Hey you!” she repeated, “come here!” she ordered.
People were starting to stare at me and wondering why a fifteen year old guy was trying to escape a cheerleader and I faltered, not sure what to do.
From around me, I heard the running footsteps of several people and turning to look, I saw to my dismay, the two hot babes from yesterday coming up to cut off my path. They looked no less stunning than they did yesterday and I noticed that the blonde’s big breasts jiggled and swayed within her tight top as she moved to position herself in front of me.
She put her hands on her micro-skirted hips in a stance of defiance and blocked my path, her beautiful face giving me a look of contempt.
“Well…if it isn’t the sniveling sissy who wet his pampers,” she sneered with disdain.
“Leave me alone,” I replied nervously as my face reddened with shame.
I tried to step around her but she moved to obstruct my way.
“Not so fast, Sissy-boy,” she said as she held up her small, immaculately manicured hand in front to halt me, “are you wearing your diapers again?”
I blushed hotly but found myself suddenly speechless.
“Leave me alone,” I repeated, sounding weak and insecure.
I tried to move around her but she reached out and grabbed me with surprising strength.
I looked down at her thin, feminine arm and I could see how toned she was. No doubt the physical workouts she practiced in cheerleading were why she was in such outstanding shape. Still, as I stared at her big, bouncy breasts, I couldn’t help but feel that she was no match for me if she should try and force me around physically. I stood at least an inch or two taller than her and even with my frail body, probably had twenty pounds on her in weight.
As if reading my mind, she suddenly pushed me back belligerently, her mocking laughter filling the air as she showed off her perfect teeth and full, sensuous lips. I stumbled back, nearly tripping, and only just barely managed to keep my balance without falling. Her friend joined her in laughing at my pathetic display and she added further insults as she slapped my thickly padded bottom.
“Come on Sissy, you’re not going to let a girl push you around, are you?”
Some other people were starting to pay closer attention and a few made jeers of their own at my expense.
The sexy blonde advanced on me boldly, pushing me again with contemptuous ease.
This time, I resisted and pushed her back but she hardly budged.
“Stop it!” I told her petulantly.
She laughed openly at my attempt at defense and then, before I knew what was happening, she advanced on me and tripped me before I could respond. I fell flat on my back and the wind was momentarily knocked out of me. Taking advantage of my prostrate form, the brazen blonde fell on me aggressively, and we locked in combat. I should have been able to throw her off but I found her to be a tenacious fighter, and I struggled weakly against her attack. I couldn’t believe how strong she was and in mere moments, she had straddled my waist, her firm, perfectly smooth thighs spread out on either side of me. She had me pinned on my back and I fought frantically to reverse her advantage but I couldn’t budge her. She smiled down at me with smug satisfaction and inched forward with her sexy legs while she fended off my flailing attacks with her slim arms. Her super short mini-skirt, which had been barely long enough to cover her pert derriere, had now ridden up to the point where I could see her white panties, a mere foot from my face. Pinned helplessly on my back, she held my wrists against the grass on either side of my head while I struggled mightily against this implacable but sexy enemy. I couldn’t believe how strong she was! Despite my best efforts, I could hardly budge her shapely frame and I wriggled ineffectually under her torso.
As she inched her sex closer to my face and she bent over to hold my wrists in place, her big breasts threatening to spill out of her thin pink crop top. It was maddening that this knockout could defeat me so easily and she flaunted her overpowering femininity before me blatantly. In different circumstances, I would have been in heaven, surrounded by the sight of her sexy smooth thighs, the intimate sight of her white, nearly sheer lace panties, and her two melon sized breasts hanging inches from my face but instead, her womanly features only served to emphasize how much of a sissy I was. It seemed like she was showing off the superiority of females by thrusting her big boobs so close to my face and it was infuriating that I was powerless to stop her.
Out of the corner of my eye, I noticed a sizable crowd had gathered to watch the spectacle and I was disconcerted to find that they were all shouting encouragement to my popular opponent.
“Come on, Sissy,” she jeered scornfully, “can’t you even beat a girl?”
I squirmed mightily but she held my wrists above my head with a grip of iron. Releasing one of them for a moment, she slapped me soundly on the cheek.
“Ouch!!” I cried out, which caused a number of onlookers to burst into laughter.
Inching up my chest until her panties were mere inches from my face, she positioned her strong, firm thighs in such a way as to hold down my arms, freeing up her own which had been holding my wrists in place. I tried to kick her with my legs but I couldn’t reach her and I only succeeded in looking more weak and foolish.
Now that her hands were free, she gripped my head by a handful of hair and with the other, delivered several stinging slaps to my reddening cheek. I cried out in pain, and tears of humiliation filled my eyes. The perfectly round shapes of her bosom and cleavage became blurred as I whimpered pitifully.
Smiling wickedly down at me, she turned her torso to be able to see behind her.
“Why don’t we see what our little sissy is wearing under his pants,” she said, the challenge obvious in her tone of voice.
“No!!” I exclaimed desperately.
I struggled wildly but I was helpless with her weight on my chest. I could feel the warmth of her sex and as I fought her, I could see her bosom shake and jiggle above my face within the confines of her thin, pink top.
After delivering another stinging slap to my face, she reached behind her and unbuttoned my pants, quickly unzipping my fly and exposing my plastic panties. A collective gasp arose from the crowd as they saw what I was wearing but their shock quickly turned to laughter as they joined the busty blonde’s disdain for my sissyish underwear. As I squirmed and wriggled, her cute brunette friend came up and helped snake my pants down my legs, further exposing the pink plastic panties and trainers I was wearing.
I fought like a demon possessed now but my opponent turned back to face me, delivering several well placed slaps to my face to quiet me down. By now, everyone was laughing at my babyish ruffled panties and my face was a bright shade of red as they mocked me. The entire cheerleading squad had surrounded us to watch one of their own defeating a helpless sissy and I was humiliated beyond words.
“Okay Sissy. I’ll make you a deal,” the beautiful blonde said provacatively as she placed her hands on her sexy thighs, “I’ll let you up when you show us what a big baby you are and wet your diapers.”
“No!” I squealed frantically but she responded by lifting my head up with a sharp tug of my hair and slapping me again hard.
I fought to keep from crying but the shame was too much.
“Please!” I begged the sexy vixen, “please let me go.”
She only smiled down at me and shook her head, readying her hand for another vicious slap.
“No please! I’ll do it! Please don’t hurt me anymore!” I wailed.
With a tremendous smile of satisfaction she leaned back and waited. It wasn’t difficult for me to do her bidding: I had been holding back for what seemed like forever and now it was like a dam bursting. The pee flowed uninterrupted, flooding my nursery print training panties and quickly soaking them. I kept peeing until a pool of warm urine had puddled around my cheeks, having nowhere else to go. I sobbed in defeat and the tears spilled down my cheeks as the beautiful blonde smiled down at me triumphantly. Bending down, she kissed me on my pouting lips, leaving her pink lipstick on me.
Everyone laughed again as she got up off me, dusting her hands together and regarding me with a smug grin.
“Better run home to your mommy, Sissy,” she told me as she laughed at me once more before sauntering off victoriously.
As I watched her sexy form walking away with her saucy gait, I couldn’t believe what had just happened. Sniffling shamefully, I jerked up my pants and ran as fast as my legs could take me back home.

When I neared my house, the full gravity of what had happened finally hit me.
When my mom found out that I had wet my third pair of trainers, I knew she’d hit the roof. My cheeks were still sore from yesterday and I just couldn’t take another paddling. I had to do something…but what? Somehow, I had to hide the wet panties so she wouldn’t find them.
Running inside, I went straight to my bedroom, tearing open my dresser drawers in the hopes that she had washed my trainers from the days previous. I was frantic with fear as I pushed plastic panties, tights, rhumba panties and rompers aside in my urgent search. I banged each drawer closed and yanked open the next but by the time I had reached the last one, I still hadn’t found them.
Where were they?! Had she not washed them yet?
I knew that my mom might choose to walk in at any moment and in my panicked state, I felt another stream of pee warm my soaking wet trainers.
“Oh!” I squealed helplessly, and I desperately tried to squeeze my legs together to stop the flow.
Just then, I spied both pairs of training pants lying in a stack by the door, on top of a bunch of diapers that my mom hadn’t put away yet.
I exhaled with relief and grabbed one of the trainers, placing it on my bed to change into.
All of a sudden, I heard my mom’s voice calling from the other room.
“Jimmy?” she called me, her voice muffled by the closed door.
Oh no! I had to get out of my wet panties quickly!
In a state of wild frenzy, I tore my jeans down, only to realize belatedly that I had forgotton to take off my shoes first. I cursed under my breath and viciously ripped them off to allow my pants to get over my feet. Everything was in a blur. Was that my mom’s footsteps coming down the hallway? No time to listen to be sure. What would she do if she caught me changing out of my trainers without telling her? It was too late to think about that.
I pulled my plastic panties down in a flash, followed by the wet and still warm training panties that were sopping wet. A trickle of unabsorbed pee ran down my leg as I threw them into the open closet and jumped into the fresh pair I had set on the bed. There was no time to find a fresh pair of plastic panties so I grabbed my old ones and ignored the pee dripping off of them. Pulling them up my legs like lightning, I heard my mom coming down the hall, for sure this time. She was only seconds from opening the door! I grabbed my jeans and stuck my feet through them, yanking them up my legs and over my plastic panties in a flurry of movement. No sooner had I zipped them up when my mom opened the door and walked into the room.
“What’s going on in here?” she asked suspiciously.
“Nothing,” I said, trying to sound innocent, but I was still fairly panting from my exertions.
“What have you been up to?” she said warily, fixing me with her withering gaze. My mom had a talent for getting the truth out of me and it was rare that I could successfully hide something from her.
“Nothing, Mommy,” I repeated, trying to get my breathing under control.
“Then what was all that noise I heard?” she continued insistently.
“Um…I didn’t hear anything,” I replied unconvincingly. My heart was beating like crazy in my chest and it took all my efforts to appear calm and normal.
“Jimmy,” she said firmly, “I don’t like liars in this house. You know what happens to little boys who lie to their mommy, don’t you?”
I gulped fearfully.
“Yes, Mommy,” I croaked.
She took her eyes off of me long enough to scan around my bedroom, no doubt looking for some incriminating evidence of my activities.
Glancing down at the front of my pants, I froze in terror. There, just where the leg holes of my plastic panties would be, I saw two huge and unmistakable wet spots where the vinyl panties had leaked through. In my haste to take them off, I hadn’t noticed it before. Now, my goose was really cooked!
I bit my lip as my mom turned to focus on the visible floor of the closet. Why hadn’t I closed that damn door?
Stepping over, she bent down to pick up the discarded wet trainers I had just taken off, holding them up before my face as clear proof of my deception.
“You want to explain this?” she said, her voice filled with ice.
My mouth hung open but I couldn’t utter a sound. My mom’s eyes naturally fell to my crotch and she yanked my pants down quicker than I thought was possible. She eyed my dry training pants and everything was suddenly crystal clear to her.
“So you thought you could hide you wet panties from me, did you?” she said as she reached over to pick up the paddle.
“I-I-I-” was all I could stammer.
“It wasn’t enough that you wet yourself like a little baby…you had to go and lie to me about it too, didn’t you?” she said as she took a seat on the bed.
Tears tumbled down my face as I shook my head.
“No, mommy,” I sobbed.
“Well, little baby,” she said tersely as she pulled my plastic panties down with excruciating slowness, “I think you’ve pretty well proven that you’re not ready to be potty trained.”
“Bu-but-” I whimpered in devastation.
This couldn’t be happening!
“Your training panties are going straight into the garbage. From now on, you’ll be wearing diapers and plastic panties, all the time.”
“No Mommy!” I wailed miserably.
She tugged my trainers down to my knees and threw me over her lap.
“I hope you like wearing diapers because that’s what you’ll be dressed in when you start school this year,” she told me as she raised the paddle high above her.
I sobbed and bunched my fists as the first swat landed on my bottom like a thunderclap.
“WAAAAHHHH!!!!” I bellowed out as the wooden instrument of my punishment bit into my tender cheeks.
I slapped the floor with my hands and kicked wildly as the paddle rained down repeatedly on my smooth, helpless bottom. Even after only four slaps from her paddle, my buns felt like they were they were being smacked with a red hot skillet and I tried to jump up to escape. My mom stopped only long enough to grab my right arm and twist it behind my back, forcing me back down submissively into position.
“Oh no, you don’t,” she growled and she rewarded my efforts with a series of hard, stinging slaps from her fearsome paddle, delivered to my waiting helpless fanny.
I bawled like a two year old and kicked some more but the panties restricted my legs and my toes danced against the floor.
I howled in pain, the tears streaming down my face as I cried and cried. She kept spanking remorselessly, bent on delivering a stinging lesson to my bottom that I’d never forget.
I gasped for breath as my buns turned three shades of red. My mom paddled me until every inch had become a hot, stinging, angry crimson, burning like two globes made of flaming charcoal. My tender cheeks had become a blazing conflagration and I knew I wouldn’t be able to sit for a week.
My pathetic attempt at potty training had been an unmitigated disaster. My mom and Susan were right, I reflected bitterly, I wasn’t ready for training panties yet and I knew that diapers and plastic panties would be my constant companions from now on. That epiphany became all the more clear as the paddle with its carefully drilled holes continued to assault my punished bottom.
At last, the terrible spanking ended.
I lay prostrate, my chest heaving as I bawled loudly, my face wet with tears. My mom lifted me up slowly but my knees were shaking and I could hardly stand. I tried to brace myself against her shoulder but she quickly rose and stormed out of the room.
“Don’t you move an inch!” she commanded me sternly.
I didn’t dare defy her and I stood there, on wobbly feet, crying my eyes out as the fire on my bottom raged on. Looking back over my shoulder, I could see the deep red color covering every curve of my sissy bottom and I sobbed all the more in self pity.
My mom returned with a tube of something in her hand and she ordered me to bend over, putting my hands on the bedpost. I heard her squirt a glob of the cream into her hand and she began rubbing it into my stinging cheeks roughly, making me burst into fresh tears. Nonetheless, part of me felt some gratitude, for soon, I knew the soothing lotion would ease the raging inferno on my posterior. I noticed it had a strange smell to it and when I looked at the label, I was surprised to read Ben-gay on it. That was odd, I thought, since I’d never seen her use that on me before.
“That should help serve as a little reminder,” she said enigmatically.
She sat me down on a ready stack of diapers and quickly powdered my front area before pinning me up securely. Strangely, the Ben-gay had initially gone on cool but now I felt a growing, but unmistakable heat, beginning to buzz on my cheeks. By the time my mom had snaked a pair a yellow plastic panties over my bulging diapers, it seemed like a swarm of bees was attacking my bottom.
“Mommy! It hurts!” I wailed piteously.
“It’s supposed to hurt,” she snapped, “that’s what happens when you try to lie to me. Maybe next time, you’ll think twice before you try and deceive your mommy.”
A fresh torrent of tears spilled down my cheeks as the fire only increased within my diapers. The cream had the effect of not only increasing, but also prolonging the stinging on my bottom and I cried like a helpless baby, stamping my feet on the floor in helpless frustration.
My mom began pulling up a pair of glittery pink tights up my legs, tugging them up and over my fat diapers while I blubbered before her. These were followed immediately by a frothy pair of white, frilly rhumba panties. Their soft satin material happily stretched to accomodate my thick, bulging diapers and my mom yanked them up and over until they covered them very prettily.
The stinging was so insistent, I danced in place as she went to the closet to retrieve one of my sissy party dresses, this time, a pastel pink satin confection with a white lacey bib across the bodice and a built in petticoat. It had a pair of peach colored lambs on either side of the bib and it completed my babyish look. Obediantly, I raised my arms to accept the humiliating garment and she dropped it over me, buttoning up the back and locking me in securely.
With a quick gathering of my hair, she tied them up into pigtails with big, floppy pink bows and led me out of my room, taking me into the living room.
“Jimmy. You are to put your nose in the corner and not move until I tell you to. Is that understood?” she ordered me.
“Yes, Mommy,” I sobbed sorrowfully.
I moved to the corner and put my nose into it like an errant four year old as I cried pitifully to myself. The intense stinging on my rump hadn’t lessened one iota and I struggled to keep from dancing in place.
I hadn’t been there for more than a minute when all of a sudden the doorbell rang.
Turning my head just enough to peek at the picture window that covered one side of our front room, I spied my cousin’s entire family waiting outside and looking in at my sissyish appearance. My mom greeted them warmly and and they streamed in to see a fifteen year old sissy, crying in his dress and diapers. Giggles and exclamations could be heard from the entire family as they stopped to stare at me.
All eight of them!!

The End (sniff)

Jimmy and his new babysitter

I could’ve died of embarrassment.
Melissa, the bossy, buxom senior from my school strode into Aunt Suzie’s living room boldly, looking me up and down disdainfully. She wore a tight pink halter top with a low scoop neckline, generously revealing her deep cleavage. Below that was a bouncy white mini-skirt and her usual high heeled pumps. It was obvious from the look on her beautiful face that she held me in contempt and it was easy to see why.
I was still wearing the pink taffeta dress my mom had put me into this morning, not to mention my hair was in pigtails with pink floppy bows and my face and nails were still made up from the visit to the salon. My shiny black mary janes contrasted with the pale pink knee high socks I had on my feet but worst of all was the thick, bulging diaper that was clearly visible under the lacy hem of my dress. It was soaking wet for the second time today and it clung stubbornly to my bottom and around my crotch thanks to the snug, shimmery, rhumba panties Aunt Suzie had made for me.
“Sis, meet my favorite babysitter, Melissa,” my aunt said to my mom.
“Nice to meet you Ma’am,” Melissa said in voice that was more polite than I had ever heard from her.
“It was so good of you to come over on such short notice Melissa. I’m glad to have the opportunity to finally meet you. Suzie’s told me so much about you,” my mom gushed.
“It’s no trouble, I can always use a little extra money,” Melissa replied.
“Well I hope you don’t mind, but I’ve got a bit of a special case here. You see, my son here is a bedwetter and a masturbator–and I’ve had it up to here with his childish behavior. I’ve got him dressed the way he’s been acting-like a little three year old girl, which I think is appropriate.”
“I couldn’t agree more,” Melissa said smugly, “he’s known as the biggest sissy in school, so it’s about time he started dressing like one.”
“Oh, one thing,” my mom said almost as an afterthought, “if he should give you any trouble, any trouble at all, you have my full permission to take down his diapers and paddle his fanny.”
Melissa pulled out of her bag a large flat wooden hairbrush and wielded it in her hand menacingly.
“Don’t you worry about that, I’ll make sure this little sissy knows who’s in charge.”
“Good, and please give me a behavior report tomorrow so I can discipline him myself when I get home,” my mom added.
I quivered with dread at the thought of being entrusted to the care of this person who I knew never liked me and constantly sought out ways to humiliate me.
“Make sure he’s in bed by seven,” my mom said as Aunt Suzie and she went out the door.
“No problem, Ma’am,” Melissa said.
I felt some small relief since seven was only a half hour away. At least there wouldn’t be too much time left for her to torment me.
“Melissa, there’s a change of diapers for him in the bedroom closet, the one’s he has on are soaked. You don’t mind changing him do you?” Aunt Suzie asked from the door.
“Not at all! I’ll get our little bedwetter changed into some nice dry diapers and then it’ll be straight to bed for him,” she answered eagerly.
They said their goodbyes and then I was alone with her. Standing with her hands on her hips, she towered over me in her high heels as she glared down at me coldly.
“Let’s get a few things straight Baby-boy,” she said sternly, “You are a sissy. You are the biggest sissy I’ve ever met in my life and that’s saying a lot. I intend to humiliate you like you’ve never been humiliated before and if that means your bottom gets blistered along the way–so be it.”
I quaked in fear and a little pee trickled out into my already soaking wet diaper.
Without a word, she turned on her heel and walked out of the living room towards my aunt’s bedroom. Her five inch heels clicked distinctly across the floor, purpose filled with determination. A moment later, she returned with a handful of thick cloth diapers, powder, diaper rash cream, and a changing pad, the latter of which she spread out on the floor.
“Sit down Sissy,” she ordered me curtly.
“M-M-Melissa?” I asked tentatively.
“You will address me as ‘Ma’am’, Sissy boy,” she said firmly as she tugged my glittery panties down my legs.
“Yes Ma’am,” I answered meekly, “but aren’t I going to bed soon?”
“I’ve got other plans for you,” she said as she began peeling my clinging plastic panties down off my wet diaper and then down my legs. She left them around my ankles and then looked down at me with a frown creasing her pretty features.
“Just look at you–wetting your diapers just like a little toddler. How old are you? Fourteen? My three year old nephew is more mature than you,” she scolded me.
I hung my head in shame, unable to maintain eye contact with her.
“Believe me, I’m going to make sure everyone knows what a big sissy you are,” she said as she unpinned the sodden diapers that were now hanging from my hips. They fell to the floor with a splat and she pushed them aside.
Doing only a cursory job of wiping my damp bottom and genitals with a baby wipe, she held my legs up in the air and slid the thick stack of fresh diapers under me. But before letting me back down, she picked up her hairbrush from the floor and swung it harshly, smacking each of my bottom cheeks soundly.
“OWWW!! OW-HOWW!!” I wailed.
Her big boobs jiggled within her top with each stinging slap of the hairbrush.
“That was just for being a sissy,” she announced with a cruel smile.
I howled in pain and kicked but she held my legs while I struggled as if I were just an infant. I couldn’t believe how strong she was!
Taking a big handful of diaper rash cream, she smeared it across my pink bottom with little care taken to ensure it was an even coating. At last she let my legs down and she powdered my penis and between my legs until a white cloud filled the air around me. Grasping my diminutive white pee-wee in between her thumb and index finger, she held it like it with obvious disgust.
“What the hell is this?” she asked mockingly.
I didn’t know what to say and I feared a spanking if I said the wrong thing so I just kind of shrugged.
“I’ll tell you what it is…it’s pathetic! But then, it goes with your prissy personality,” she laughed scornfully, showing off her beautiful teeth and sensual lips.
“But don’t worry, I’ve got just the thing you can prove to me that you’re good at.” Reaching into her bag, she pulled out her monster sized strap-on dildo, its fleshy veins bulging from around its thick shaft.
I whimpered in fear as she pulled the thick, constricting cloth between my legs and pinned it tightly on either side. The bunny soft diaper caressed my skin as she yanked my still damp plastic panties up my legs. She had to wrestle with them to get them over the fat, bulging diaper but at last, it was all contained.
“There, at least you won’t be wetting on the furniture now,” she said scornfully.
Taking the dildo in her hand, she squeezed the rubber balls that were attached to the base and buried the head into a jar that I couldn’t see the label of. When she released her hold on the balls, I heard a slurping sound as the dildo sucked up whatever was in the jar like a bulb enema.
Taking off her skirt, she fastened the heavy rubber phallus in front of her, cinching up the straps around her hips and between her legs. After adjusting the fit, it stuck out from her groin obscenely, and I felt my bottom puckering in anticipation and fear.
“On your knees,” she ordered me, “time to practice your cock sucking for your future mate.”
I blushed and rose to my knees as I stared at the leviathan pointing at my face. The end of it was now covered in a milky white substance from the jar and I could only wonder what it was.
“Ma’am?” I tried to say but as soon as I opened my mouth, Melissa shoved the slippery dildo straight past my lipstick covered lips, choking me with it. My hands wind milled in the air and my eyes went wide open as I squealed in distress. My mouth was filled with the giant rubber cock and I was forced to taste and swallow the creamy substance that covered the end of it. It tasted somewhat salty and I gagged several times as she rammed the dildo forcefully in and out of my mouth. My checks were stretched wide trying to accommodate the massive cock and she hammered the back of my throat with the bulbous tip.
“That’s right Sissy, suck it like a good little boy,” Melissa said mockingly as she thrust her hips forward and humped my aching mouth, “this is what you’ll be doing from now on. I’m just getting you trained for the real thing.”
I slurped and slobbered at the dildo as it slid in and out of my mouth. She never took it out enough to leave the head exposed before she plunged it back in as far as it would go. She went on at a moderate pace for about ten minutes and then she began to speed up.
“Get ready Sissy-boy, I’m about ready to cum, so that means you’d better get ready to swallow!” she snickered.
I moaned and whimpered as she pumped me back and forth until at last, she drove the dildo all the way into the back of my mouth and squeezed the ball sack. I felt creamy goo shoot into my throat and mouth and I struggled to avoid gagging.
“Better swallow every drop or you’ll be going over my lap, Sissykins,” she warned me as she held it firmly in place. Her hands gripped the back of my head firmly, preventing me from any escape.
I did my best to swallow but then she squeezed it again and more of the cream shot into my mouth, filling it with that salty taste again. I squealed like a little girl, my rouged cheeks bulging outward already from the gargantuan head of the cock as I swallowed again and again.
At last, she pulled the dildo from my mouth and I gasped and heaved, trying to gather my breath.
“Yes, that was quite a workout, wasn’t it?” she said with a smirk, “and now it’s time for you to assume the other position you’ll be finding yourself in, more and more. This one should be very natural to you.”
She pulled my plastic panties down and left them hanging on one ankle. Then she grabbed a few cushions from the couch and a pillow and put it in a pile on the floor. Grabbing me roughly, she maneuvered me over the pillow, bending me over it so that I was face down and my fanny stuck up in the air. She unpinned my diaper and pulled it back, exposing my sticky bottom, still slathered with white diaper rash cream. I whimpered fearfully as she opened a jar of vaseline and buried the strap-on into it, coating it generously before positioning herself behind me, on her knees. I felt a greasy finger poking into my puckering anus and I squealed again in panic.
“Better get used to this Bedwetter-boy, ’cause all you’ve got to look forward to for the rest of your life, is some stud humping you in the ass with his big cock. You have no business in a woman’s bed but maybe you can learn to please a man,” she said as she slipped a glob of vaseline into my hole.
“Please…please don’t, Melis-Ma’am,” I wailed, correcting myself at the last moment.
Ignoring me, she positioned the greasy head of the dildo between my cheeks, while simultaneously spreading them apart with her hands.
“No…no…no…please, please,” I begged her piteously. My dress and petticoats had slid down and out of the way, gathering under my arms as my bottom pointed upwards, perfectly positioned to receive Melissa’s big strap-on.
Fishing with the thick shaft, she directed it firmly at my hole, applying steady pressure with her hips while I struggled to try and escape. With her other hand, she reached over and grabbed her hairbrush, bringing it down in several harsh slaps to my naked, exposed fanny. Beating my bunched up fists against the floor, I wailed helplessly as I received my punishment.
Miraculously, the huge head finally slid past my sphincter and I sobbed in defeat.
“There,” she said satisfied, “now, you’re getting what you need.”
Tears of humiliation trickled down my face as she slowly pushed the dildo in deeper and deeper, at last, bottoming out far inside me.
“Feel that Jimmy? That’s what a man’s cock feels like when he’s taking you like his little girl. Don’t you feel full and satisfied?”
“No Ma’am,” I whimpered between sobs.
My hole felt like it was being stretched apart and I breathed heavily as I struggled to try and accommodate the massive dildo. She slowly withdrew it but then pushed it right back in again. I moaned deliriously as she began a slow steady rhythm, in and out, thrusting it deep into my rectum. She grasped my hips and held me tightly, preventing me from escaping her burrowing strap-on and forcing me to experience every millimeter of the titanic dildo. As if to echo her demeaning words, I sounded like a little girl getting humped, my high pitched voice squealing and moaning in synch with her thrusts.
Occasionally, she would stop long enough to take a smack at my bottom with her hairbrush before resuming her pumping. My poor anus ached and my fanny stung after five minutes. After ten minutes, I knew I’d be having difficulty walking normally.
At long last, she drove the dildo as far in as it would go and squeezed the ball sack, filling my rear end with another load of the creamy substance she’d refilled into the strap-on. As she withdrew it, I lay on the floor panting and heaving, exhausted from her efforts. I felt her pull the back of my diapers up and re-pin them tightly. Rolling me over, she held the leg hole of my pink plastic panties open and snaked them up my ankles and thighs. Gazing over the top of the gathered ruffles and lace of the hem of my party dress, I watched as she tugged the panties up and around my diapers. Unexpectedly, I felt a gooey substance of my own in the front of my diapers. Had I cum and not even realized it? I blushed deep red at the thought and glanced up at my beautiful babysitter who was ignoring me. She seemed so powerful and strong to me. Yet, she was also one of the most gorgeous girls in my school. I feared her, yet I couldn’t help admiring her every sexy feature.
She un-strapped the dildo and put it on the floor beside me.
“Clean that up,” she ordered me tersely.
“Yes Ma’am,” I replied obediently. There was no question in my mind who was boss around here. I got up shakily on my feet and had to waddle off to the bathroom slowly, partly because of the thickness of my diapers but also because my butthole ached from the long and thorough reaming I’d just received.
When I got back into the front room, Melissa was just hanging up her cell phone.
“Come here Sissy, let’s get your prissy panties on, it’s time to go,” she said as she held my rhumba panties open for me to step into.
“Huh?!? Where are we going?” I quaked.
“We’re going to a little party, you and I,” she said with a smug look, “so I want you dressed as pretty as possible.”
I immediately started pouting but Melissa would have none of it.
“Come on Sissy-boy. You’re coming whether you like it or not. The only difference is whether you leave here with or without a spanked bottom,” she informed me impatiently.
I stomped my feet in frustration as I reluctantly put one foot at a time into the panty leg holes, allowing her to slide them up my hairless thighs and over my pink plastic panties.
“But my mom said I was supposed to go to bed,” I whined.
“I don’t care what she said,” Melissa said as she unrolled a stick of pink lipstick from her purse, “it’s time people started seeing you as the prissy sissy that you really are.”
It was all so unfair!
As I pouted like a four year old, she applied two thick coats of pink glossy lipstick to my lips which had lost most of their previous coating on her strap-on dildo. She handed me a big bottle of warmed milk and ordered me to finish it so she could refill it before we left. Looking at her big breasts within her tight halter and seeing the determined look in her dark eyes, I knew better than to refuse. I sucked from the bottle teat until only air bubbles came out. She snatched it out of my hand and quickly refilled it, zapping it in the microwave before returning it to me.
“Okay, let’s go,” she said as she grabbed her keys.
I wanted badly to stand up to her but the idea of defying her was just too frightening. I knew she wouldn’t hesitate to yank my diaper down and paddle me severely and then I’d still have to do whatever she wanted anyway. In addition, I knew she’d tell my mom and I’d face another hard spanking in the morning. My bottom had already been paddled numerous times within the last 48 hours so the last thing I wanted to do was to tempt my stern babysitter.
Swallowing what little pride I had left, I followed Melissa out to her car, dressed like a three year old girl still in diapers.

We drove for about twenty minutes in which time I had finished (with some persuasion) my baby bottle of milk. Melissa pulled into the parking lot of a busy AM/PM store and told me in no uncertain terms to get out and purchase some more milk from inside. I begged and pleaded with her not to make me go in dressed like I was but I gave up when she retrieved her hairbrush from her bag. Fearfully, with my empty bottle in hand, I stepped out of the car tentatively, which she had parked right in front of the store’s main door. As I passed cautiously by the hood of Melissa’s car, she honked her horn loudly, and I gasped as everyone inside and out in the parking lot turned to stare at me. From behind the wheel, I could see Melissa laughing uproariously at my predicament and I blushed a deep shade of red.
With tears of shame in my eyes, I opened the glass door and walked inside. All eyes were on me and a buzz of conversation erupted from the patrons. Sniffling to myself, I waddled over to the drink case and quickly grabbed a carton of milk. The lace on the leg holes of my rhumba panties kind of tickled my thighs and I tried in vain to pull my dress down to cover them. There was really no point though, because the hem of my party dress only covered the waistband of my panties and diapers. Everyone stared at the ruffles adorning my thickly padded bottom and several young women giggled aloud at me.
“Oh my god!” one exclaimed as she stared open mouthed at me.
“Did mommy’s wittle baby run out of milk for his ba-ba?” another asked.
I tried to ignore them but I could feel my ears getting hot and my cheeks burning fiercely in shame.
Facing the woman behind the counter, I placed the milk and my empty bottle next to the register.
“I’m supposed to ask you to warm this in my bottle,” I mumbled under my breath to the saleswoman.
“Sure Honey,” she replied with a wink as she took the carton of milk and poured it into my baby bottle. She walked over a few feet and placed it into the microwave, setting the timer on for half a minute.
I stared straight ahead trying to shut myself off from what was going on behind me but all of a sudden, I felt the seat of my diapers getting squeezed in someone’s hand.
“Oh!” I cried out in sissyish surprise.
“Looks like baby hasn’t wet herself yet,” one of the young girls behind me said with a smirk.
“What a sissy!” the other said disgusted.
“Leave me alone, please,” I said meekly.
The second one repeated what I said in a mocking tone.
“Leave me alone, please,” she sneered.
“Little sissies like you shouldn’t be out this late. It’s past your bedtime,” the first one warned me.
Just then the dinger on the microwave went off and the lady handed me my milk. I snatched it out of her hand and bolted for the door but not before one of the girls slapped my diapered bottom as I went past her. Their laughter rang in my ears as I ran for Melissa’s car, tears filling my eyes.
When at last I was back in the passenger seat, she was still laughing at my spectacle.
“I want you to make sure you finish that before we get to the party,” she told me once she was able to contain herself.
“But I’m not thirsty,” I complained.
“Maybe you’d like another session with my strap-on before bed, hmm?” she threatened me.
“No Ma’am!” I replied quickly, and immediately began sucking from the nipple of my bottle.
As we made our way across town, I could feel the milk sloshing around in my stomach and the first indications that I would have to go pee soon. Maybe I’d be able to sneak into a bathroom when I got there, I tried to tell myself, but I didn’t think that was very likely. Much more likely was that Melissa would force me to wet my diapers in front of a number of people. The thought made me cringe with anxiety.
We parked along the street and got out near the house that was having the party. I could really feel the pressure in my bladder now that I was standing and I walked slowly behind Melissa down the sidewalk. Her heels clicked with self assurance as she led me up the driveway toward the house and I noted the sensuous curves of her calves and her powerful, but smooth thighs above them. Like her or not, she certainly was all woman.
She rang the doorbell of the house and a pretty teenager answered, another one of the girls from my school. She saw Melissa and was about to say something but then she caught sight of me and broke out into gales of laughter. Pointing at me, she slapped her hand on her knees as she doubled over, her humor consuming her.
I felt like I was wilting, still standing out on her sidewalk where everyone could see me and it didn’t feel any better to have another one of the school’s cheerleaders laughing her butt off at me. When she could finally speak, she called out to her friends inside to have them come take a look. The hallway behind her filled up with young women as they took a look at me and joined the first one in laughing loudly at my appearance. I was completely humiliated and I couldn’t help it, tears started streaming down my face.
Most shook their heads at me but a few others started mockingly try to comfort me.
“Aww…come on inside baby, we’ll get you a new ba-ba.”
“Did the wittle baby wet her diapies?”
“Poor wittle sissy, he just needs a diaper change.”
We went inside and I felt several hands squeezing the thick seat of my diapers. My bottle was taken from me and I was led into their living room and made to sit down.
Strangely, I noticed some lights set up and an area cleared out in one corner of the room.
“Melissa, you’re just in time, the show’s about ready to start,” one of the girls told her.
Some dance music started and from an adjoining room, one of the school cheerleaders came out. She was wearing a white push up bra, high cut panties and high heeled sandals, and she sashayed out with a sexy walk, modeling the outfit for the girls present. I had never seen a girl this undressed except for a Playboy magazine I’d been shown and I was completely mesmerized.
Another girl started describing the outfit, who made it, and how much it cost. Apparently, this was one of those lingerie parties I’d heard about but until now, had never dreamed I’d actually see one. Watching the sexy girl saunter around, swinging her hips in a sassy way, I felt my little pee-wee start to harden. I couldn’t believe how erotic she was, and the soft folds of my diaper only increased my excitement.
Melissa sat down near me and handed me my bottle which was once again filled with warm milk.
“Better finish that in the next five minutes,” she ordered me.
“Yes Ma’am,” I said quietly.
Several of the girls looked at me and giggled so I kept my eyes downcast.
The next girl that was modeling came out in a black bustier, her substantial breasts spilling over the top creating two delicious mounds and a deep cleavage. The girls around me ohhed and ahhed and unconsciously, I found myself rubbing the front of my diapers.
“Go get me a beer out of the fridge,” Melissa demanded.
“Yes Ma’am,” I replied.
As I got up slowly, I could feel the insistent pressure on my bladder ready to burst. I limped slowly to the kitchen but a trickle slipped out and into my diaper. Crossing my legs, I danced in front of the refrigerator but the effort was too much. In a moment, I was flooding my diaper, peeing uncontrollably as I sobbed in defeat.
I felt someone patting my pantied bottom and turned to see the first model smiling down at me.
“There, there little boy, wet your diapers like the big sissy you are,” she said soothing, yet patronizingly.
I pouted helplessly as I continued wetting, the pee saturating the front and seeping down between my legs. As more and more pee went into my diaper, the seat started taking the excess and I felt the wet cloth pressing against my cheeks.
“Why don’t you come out into the living room now and tell your babysitter what you just did,” she said as she patted my bottom gently.
I shook my head no pleadingly but she just nodded and took my wrist, leading me into the other room. I waddled out behind her, my warm, wet diapers clinging closely to my skin.
“Excuse me ladies,” the scantily clad cheerleader said to her gathered friends, “but Jimmy here wants to make an announcement.”
I shook my head no but she squeezed my wrist painfully until I acquiesced.
“I, um, kind of, um, wet myself,” I mumbled almost inaudibly.
“Speak up, we can’t hear you!” the busty model wearing the black bustier shouted.
“I said, I wet my diapers,” I said, barely louder.
“We still can’t hear you!” several others chorused.
“I wet my diapers!” I practically shouted in exasperation.
The room broke out in gales of laughter and my ears burned with the sound of it. Hot waves of shame washed over me and a tear trickled down my cheek. These pretty girls all realized by now that I was nothing but a diaper wetting sissy, no better than a two year old toddler. As I looked around the room, I saw that the only girl not laughing was Melissa. She was staring at me with a stern look on her face and I felt my knees get weak as I watched her take her hairbrush out of her purse.
“Michelle, it looks like I have a little business to take care of here,” she told her friend as she pulled a straight backed chair out into the middle of the floor, “can someone get me a towel to put over my lap?”
Within seconds, a girl returned with a towel which Melissa draped over her lap. Several girls behind me started pushing me towards her but I tried to resist them, digging my mary janes into the carpet and putting my hands out. They easily overcame my efforts and I stumbled next to Melissa who was gazing at me with unconcealed disdain. Seeing the cold look in her beautiful eyes and the hairbrush in her hand, I let go with another stream of pee into my diaper as I trembled in panic.
“I think the problem your mommy is having at home is that she doesn’t punish you when you wet yourself,” Melissa told me as she yanked my glittery rhumba panties off my diaper and down my skinny legs.
“No Melis–Ma’am, please don’t spank me,” I begged her in desperation.
“Maybe if you got your bottom paddled every time you wet your diapers, you’d learn to grow up,” she continued.
“Please, please don’t, I couldn’t help it,” I whined.
“Well tonight, I’m going to help you grow up a bit,” she said as she peeled my pink plastic panties down my thighs past my knees.
I whimpered as the girls all got themselves comfortable to watch me get soundly spanked. I stared down the dark line of cleavage between Melissa’s big boobs as she tugged me over her lap. Meekly, I situated myself so that my fanny was properly available and she began unpinning my soaking wet diapers, commenting to others about them.
“Do you see why his mommy has to put him in such thick diapers? Just look at how much he’s peed into these.”
The girls within my field of view shook their heads in disgust at my childish display and my face turned a deep shade of red.
Melissa pulled back the sodden cloth and pushed it between my legs. I waited fearfully for the first smack of the hairbrush but Melissa reached over and grabbed my right arm, forcing it up behind my back painfully. I squealed in protest to which the girls all laughed at again.
The first hard slap of her hairbrush landed squarely on my damp cheeks with an electric shock. I howled in pain and she smacked me again in the same spot. As I kicked my mary jane clad feet in helplessness, she spanked me harshly, slapping my cheeks in a punishing rhythm. Almost immediately, I burst into tears and I struggled frantically to get off of her lap. My efforts were in vain because she only held my arm firmer and spanked my bottom harder. I wailed like a three year old as the girls around me smiled, some nodding their heads as I got the just punishment they obviously felt I deserved.
The wooden hairbrush landed again and again, turning my fanny into a blazing red hot bed of coals. I sobbed and cried, the tears streaming down my face in profusion and my breath coming in short gasps. Each angry slap of her hairbrush made me think I wouldn’t be able to stand the next but then it would land and I would cry out even louder. I looked through tear filled eyes at her high heel pumps, which easily supported my light weight, despite all the flailing around I was doing.
As I bawled like a baby, I realized with certainty that I really was just a big sissy. I knew for certain that my future would be filled with wet diapers, dresses, and hard spankings for the discipline I so badly needed.

Jimmy’s day of Shopping

I woke up in a strange state of arousal.
As I rolled over on my waterproof mattress cover, my hand went down to the thick front of my diapers and felt, to my surprise, that I was still dry. This was highly unusual because I had been waking up every morning for the past two months with my diapers consistently soaked. As I mused over this sudden change, I stroked the surface of my plastic panties encasing the soft diapers. It didn’t take much for my little weiner to become hard and I found myself secretly enjoying my baby soft underwear. My mom insisted on dressing me in cloth diapers rather than disposables, and when she washed them, she used a lot of fabric softener which made them get softer and softer with each washing. As a result, I found myself being constantly caressed by the fluffy diapers and despite my humiliation at having to wear the infantile clothing, my wee wee sought relief.
I had been masturbating covertly for several years now and getting away with it because I found that when I wet myself, the evidence of my misdeeds would be covered up. And so far, my mom hadn’t caught on to my recently discovered sinful pleasures. Most often, my fantasies centered around my voluptuous and pretty teacher, Ms. Taylor, although yesterday’s humiliating spanking in class at her hand certainly had curbed any remaining illusions I had about her feelings towards me.
This morning, I swung my legs out of bed and sat up, to be able to stroke myself more comfortably. For some strange reason, I found my mind wandering back to yesterday’s traumatic event at school in the girl’s bathroom. That was where Melissa, a tough yet beautiful senior, and her bullying girlfriends had forced my inside and then humped me senselessly with a big strap-on dildo.
At the time, I had found the experience to be initially painful, not to mention, extremely embarrassing. I had been forced to endure a long and slow humping as Melissa held me down and forced me to take in every inch of her dildo. I was crying tears of shame by the time she finished, but now, in the safety of my bedroom, I recalled the experience with a strange sense of arousal. I couldn’t yet identify my feelings but somehow, when I remembered looking into the big mirror on the bathroom wall, my weiner stirred in my diaper. I thought of my tormentor, Melissa, tall, demeaning, big breasted, and dominating. I remembered her big boobs heaving within her tight, stretchy top as she pumped me from behind with her dildo. But in my secret heart of hearts, I found myself wishing she were here right now, bending me over my bed to hump me again. I blushed at the very thought of it but I couldn’t escape or deny the way I felt.
As I stroked the front of my soft diapers, I was reaching a new height of ecstasy, oblivious to my surroundings, when all of a sudden, my mom burst into the room unannounced.
“WHAT-ON-EARTH-IS-GOING-ON-HERE!!?” she demanded angrily.
My mouth dropped open in shock and surprise as I tried to stammer out a response but I couldn’t think of anything even remotely plausible.
“I-I-I…I-um…ahh…I was just…ah,” I bleated out nervously.
“Young Man. You are NOT to masturbate in this house! Do you understand me?!” she demanded as she shook her index finger threateningly at me.
“Yes Mommy!” I quickly responded, fearing her imminent wrath.
She seized my wrist and yanked me up while simultaneously reaching for the paddle, an oval instrument made of hard oak with holes drilled in its face to provide extra sting. I knew from past experience just how painful it could be when applied to a naughty bare bottom. I quaked with fear as she sat in the only chair in the room and began yanking my plastic panties down.
“No Mommy! Please! I won’t do it again!” I begged her piteously.
“Jimmy. You’ve had a good hard spanking coming for much too long now. It’s time for you to have yourself a good cry,” she said tersely as she tugged my panties down past my knees. I whimpered and pleaded but she pulled me over her knee, unpinning my diapers with practiced ease. I was all too familiar with this position and knew there was nothing that was going to save my bottom from being severely paddled. Even before the spanking began, I burst into tears, squirming on her lap as she held me firmly in place with her left hand.
I wailed in response and kicked my feet wildly, gyrating on her lap as the paddle swatted my tender bottom with harsh, angry slaps. All thoughts of the beautiful but domineering Melissa vanished from my mind as I focused on the punishment being metted out to my youthful cheeks.
“Naughty boy!”
“Naughty little sissy!”
I howled in pain and anguish as I struggled, kicking my feet and beating my fists against the floor. Tears streamed down my face as I cried and sobbed like a baby.
“You are NOT to use your diapers to masturbate in! Do you understand me??!” she demanded. Without giving me a chance to respond, she continued my paddling without pause.
Suddenly, she stopped abruptly and rested the paddle against my blazing bottom. I couldn’t see them, but I knew my cheeks were now a bright shade of red.
“How long have you been playing with yourself?!” she demanded.
Between sobs, I tried to save myself from any further punishment.
“Ne-ne-never. I never have before,” I stammered uncertainly in response.
The paddle swooped down again and again, blistering my bottom in its avenging mission.
“OW-WOW-WA-WAHHH!” I cried desperately.
“How long have you been playing with yourself!” she repeated angrily.
“A-A-A couple ye-years,” I admitted tearfully, between gasps for breath.
The paddle came down again and again, stinging my poor fanny mercilessly.
“And how often do you masturbate each week?” she asked, holding the paddle up high over my crimson behind.
“A-a-couple times,” I replied. I knew it was foolish to try and lie now.
The paddle came down again repeatedly until I was sobbing and completely defeated, my face wet with tears. She made sure that my fanny was thoroughly punished as she spanked me good and hard, swatting every square inch until the sides glowed a cherry red like the center. Finally, I felt her pin my diapers back in place over my stinging bottom and stand me up. Bawling like a baby, my shoulders heaved and I tried to rub my burning cheeks through the thick cloth of my diapers. My mom ignored my efforts and yanked my pink plastic panties back into position where they effectively sealed the fire within. I shifted my weight from foot to foot as the inferno on my backside continued to build.
After hanging my paddle up on the wall where it belonged, my mom took off my nighty and replaced it with the petticoat aunt Susie had put me into. I sniffled miserably as she followed it up with the fluffy pink taffeta dress with white lace, pulling it over and adjusted the hem. Wordlessly, she she sat me on my bed and began pulling my knee socks on, followed by my mary janes. I watched her with sinking heart, my legs bowed out at an angle from the thick diaper between my legs.
“Maybe dressing like a little sissy baby will make you want to grow up and start acting like a young man again,” she said tersely.
I sniffed in self-pity as she stuffed a big pacifier between my lips and put the loop around my neck. Today, I was determined not to wet my diapers since I didn’t want to prolong this treatment any longer than was absolutely necessary.
My mom took me into the kitchen and made my breakfast while I shifted in my seat. I just couldn’t get comfortable despite the multiple layers of soft diapers, my bottom just stung too much.
“Quite fidgeting,” she ordered me as she put my oatmeal before me. I was glad she wasn’t going to feed me too. From somewhere, she produced a large baby bottle with warm milk in it. I scowled but knew better than to refuse it.
“That’s right Jimmy,” she said as if reading my thoughts, “there are going to be a few changes around here that you better get used to. We’re going shopping today to pick up a few items that you’ll be needing.”
I was afraid to ask what those would be so I said nothing.
“Before, I was prepared to keep your diapers hidden under your pants but now, it’s clear that stronger measures are necessary. From now on, your diapers and plastic panties will be on display for everyone to see them. I’m going to make sure everyone sees just what a big sissy baby you are.”
I cried softly to myself as I looked forward to a day full of humiliation and shame.
A moment later, the phone rang and my mom answered it. Apparently it was my aunt and after a brief amount of small talk, my mom eyed me curiously.
“Hold on Sis,” she told my aunt as she dug in one of the kitchen drawers. Taking out a measuring tape, she came over to me and told me to stand up. As I did so, she measured first my waist, then the widest part around my diapered hips, then the diameter of my legs where they met the elastic of my plastic panties. My heart skipped a beat as she read the measurements to my aunt. What could she want them for, I wondered. I knew her to be skilled with a sewing machine and I could only imagine what she might be making for me.
My mom smiled at me with a ‘just you wait’ kind of look on her face before she said goodbye to my aunt and hung up the phone.
After I finished breakfast, my mom told me to go brush my teeth and get ready to go. I pouted in frustration as I did so, being unable to avoid looking into the mirror and seeing my embarrassing reflection. I couldn’t believe how sissyish I looked, with my ruffled pink plastic panties peaking out beneath the masses of white ruffles from my petticoat and dress. There was absolutely no way I’d be able to hide them from anyone who saw me.
My mom soon joined me and she re-brushed my hair, lifting each side into a pair of sassy pigtails and securing them with pink floppy bows.
“There. Take a look at yourself,” she said, turning me back towards the mirror, “now you look like the way you’ve been acting.”
A tear formed in my eye as I looked at the diapered sissy baby staring back at me. As if to complete the picture, my mom stuffed my pacifier back into my mouth.
“Come on Baby,” she said as she slapped my thickly diapered bottom, “it’s time to go.”
I heard the jangle of her car keys and then the realization really hit me. I was going to go out in public dressed like a baby!
“No Mommy! Please! Please don’t make me go out like this!” I wailed as my pacifier fell out of my mouth.
She frowned down at me before jamming the pacifier back in.
“Come along you little sissy, we’re going shopping whether you like it or not.”
She dragged me forcefully out the door and in my state of panic, I felt a sudden stream of warm pee escape into my diaper.
“Nooo!” I whined pathetically.
My mom yanked my forward with her left hand and at the same time, her other hand swooped down to swat my behind.
It didn’t really hurt but I cried out anyway. Worse yet, another stream of pee followed the first one, creating a large wet spot in the front of my diapers.
Dragging me by my wrist, my mom put me in the back seat, securing my seatbelt like I was still a child. The seatbelt rode over the top of my diaper, pulling my dress up and completely exposing my plastic panties to anyone who should look in. Lastly, she placed my pacifier back into my mouth and warned me not to remove it unless I wanted my bottom warmed again. I certainly didn’t want that, so I sat there sulkily, pouting as I sucked the rubber nipple.
We drove out of the neighborhood and then through town, moving in and out of slow traffic. At one point, I looked over to see a van of girls staring at me and giggling and I blushed a deep shade of red. It didn’t help matters that my diapers were already wet and worse, I felt my bladder needing further relief. How was I to hold out the rest of the day? I wondered nervously.
Finally, we pulled up in front of Babys-R-Us and my mom got out to open my door. I noticed here in town, a strong breeze was blowing and no sooner did I get out of the car when the wind picked up the back of my dress and petticoats, fully exposing my diapered fanny to a family close by in the parking lot.
“OOHhmmmph!!” I squealed through my pacifier as I fought to get my dress under control. The mother of the other family looked at me strangely and I felt myself blushing again. As they walked by, her daughter, a little girl of about five pointed at me and blurted out, “Mommy, why is that boy wearing diapers?”
“I don’t know Katie, now come along,” she said as she took her inside of the store.
I was so ashamed I felt like crying.
We went inside and I gazed around at the vast showroom of baby furniture and supplies. There were all manner of cribs, toy sets, playpens, changing tables, not to mention a section dedicated to clothing and diapers.
My plastic panties crinkled loudly in the quiet store, announcing my presence as plainly as a set of bells, and an older, matronly woman came over to assist us. She looked very severe with her hair pulled up into a bun and her conservative clothes. She eyed me with suspicion but greeted my mother warmly. I sucked my pacifier nervously as I was unable to hold eye contact with her.
“And how can I help you today?” she asked.
“Well, we have a small problem,” my mom began, “you see, this morning I caught my little baby here masturbating. So for starters, I need a playpen that I can put him into where I can keep an eye on him.”
I blushed furiously at this admission to a total stranger and when I glanced back up at her, she was staring at me harshly. I had the feeling she would spank me herself if given even the slightest encouragement and I shifted from one foot to the other in anxiety.
“A little masturbator, eh?” she said disainfully, “well, I think we can find something that will keep him out of trouble. Come right this way.”
She lead us down an aisle of larger baby furniture until we reached a number of playpens. She waved her hand at one that had a padded vinyl floor with nursery print characters decorating it. The sides were made up of a soft netting that went to pink padded side rails, about three feet off the floor.
“This would be good,” my mom commented, “this way I can place him in here when I’m busy around the house and keep him where he can be constantly supervised. Now, it seems to me that a baby in his playpen needs to have some toys otherwise he might be tempted to play with something else. Isn’t that right Jimmy?”
Reluctantly, I nodded my head but kept my eyes downcast.
“Perhaps your little baby would like some dollies to play with?” the saleslady suggested. She took us to the toy section and they picked out a “Little Miss Wettums” doll, one that still wore diapers and would wet them at random intervals.
“Maybe that will help remind you of your own wetting habits, Jimmy,” my mom informed me.
I also got a set of blocks and a rattle before the subject returned again to my masturbating activities.
“Tell me your opinion on this,” my mom asked the stern lady, “I’ve been thinking about placing him into diapers that are scratchy and uncomfortable to discourage his naughty behaviour…what do you think?”
“Personally, I think that would be the wrong direction to go in,” she said very firmly, “what’s happening, is that your baby here simply can’t resist temptation. You dress him up in a thick, soft diaper and he feels it’s a tool for him to play with himself in. Now, you could put him into something much more uncomfortable but then you’ll just be avoiding the issue. The fact is, your little sissy here is going to be confronted with temptation all his life so you need to nip his bad habits in the bud, early on. He needs to be taught that masturbation is unacceptable and will earn him a trip over your lap immediately.”
“-Believe me, he got his little fanny soundly spanked this morning when I caught him,” my mom assured her.
“Good. That’s the first step. If this little sissy were under my roof, he’d soon be cured of his masturbating nonsense. I like to spank first, then ask questions later.”
I squirmed uncomfortably at this discussion of how often and where my bottom should be paddled.
“No,” she said continuing, “what you need to do is to control his environment while still exposing him to temptation. Put him in the softest possible diapers and use plastic panties that are thin and soft. Come and let me show you.”
The lady took us down another aisle to a section containing rubber and plastic panties.
“This brand of plastic panties are baby soft, and they come in some wonderfully cute colors.”
I watched as my mom selected numerous pink, yellow, lilac, peach and a few white ones.
“The idea is for him to be put into a position where he’ll be tempted to masturbate but he won’t be able to. And if he does, that’s when it’s time to pull his diapers down and paddle him until the little sissy is bawling like a baby. You see, he just lacks discipline in his life. When you’ve cured him of his masturbatory games under those conditions, you’ll know that he’s able to resist temptation elsewhere in life,” the lady explained carefully.
“That’s an excellent suggestion,” my mom agreed with enthusiasm, “thank you very much.”
“It’s no problem at all, I’ve been disciplining bedwetters and masturbators for years now.”
“I was wondering, perhaps you wouldn’t mind babysitting for me on occasion? You seem to be just the kind of person I’m looking for and I’m still trying to find someone that can help out when I’m out of the house.”
“I’d be happy to,” the lady said quickly as she gave me a look of determination that made me shiver, “I’ll have him singing ‘the Good Ship Lollipop’ by the time you get home.”
My mom laughed at that and she took down the lady’s phone number.
“Now, no sissy’s wardrobe would be complete without nursery print panties. I like this brand because they have little plastic lace accents around the legs and waist. They’re very babyish-wouldn’t you agree?”
“Oh yes, very much so,” my mom agreed. She took a pink pair and held it up to my diapers, imagining them on me.
“Yes, you’ll definately be wearing these on a regular basis, Jimmy,” she assured me.
I wilted at the thought of being dressed up in the humiliating panties.
“Now these aren’t quite as soft as the previous brand I showed you but they’re good when he’s out in public. Under those circumstances, you won’t have to worry about him masturbating anyway,” the lady explained.
“Yes, that makes sense,” my mom agreed.
The two continued to fill my mom’s cart with other items as I watched with growing dismay. I was only half paying attention when I caught sight of another woman entering the store. My mouth dropped open in shock as I watched her pick up a basket and walk alongside the first row of baby toys. Even from a distance, I immediately recognized the distinctive form of my teacher from school, Ms. Taylor. Her long brown hair, her prominent bosum, flat tummy and long legs all seperated her from the average woman. And then the familiar ‘click-click-click’ of her high heels that was indelibly burned into my memory reached my ears. I felt the blood rushing to my ears as I saw her turn down our aisle, making her way slowly towards us as she shopped without looking up. Immediately, my heart began beating furiously as my mind scrambled with what to do as she grew closer and closer to us.
I turned slightly so I could watch her out of the corner of my eye. Please don’t come down here, I silently beseeched her, PLEASE.
Ms. Taylor picked up a stuffed animal and then set it back down, slowly making her way towards us. What was I to do if she saw me? What would I say? I had no idea. I suddenly felt the need to pee stronger than ever and it didn’t help that my diapers were already wet. I fidgeted around trying to postpone the inevitable.
“Jimmy, stand still,” my mom chided me.
I bit my lip nervously as I turned my back towards Ms. Taylor who was now within ten feet of us.
My bladder muscles, never very strong, decided at that moment to relax. A strong rush of warm pee flooded into my damp diapers, completely saturating them before I could stop it.
“Oh!” I cried.
I shifted from one foot to another and whimpered to myself as my diapers grew heavier and started to sag from the weight. The stern saleslady noticed it too because she stopped talking to my mom and stared down at me harshly.
“Looks like your little baby just wet his diapers,” she commented, louder than was necessary.
I blushed a deep red as my mom turned to me and lifted up the hem of my dress and petticoats to get a better look.
“Jimmy? Have you wet your diapers already?”
Just then, with the worst possible timing, Ms. Taylor appeared next to me and she looked down, her mouth open in surprise.
“Jimmy? Is that you?” she asked in shock.
I looked away in utter embarrassment as the warm pee started to seep into the seat of my diapers. I couldn’t believe my incredibly terrible luck to be seen by my pretty teacher, dressed like a little girl and wearing a very wet diaper. During the pause in conversation, a last burst of pee streamed into my diaper, forming a puddle in my crotch before slowly soaking into the saturated cloth.
“Jimmy. Where are your manners?” my mom said insistently, “answer the nice lady.”
“Jimmy?” Ms. Taylor asked again, “I didn’t uh-recognize you at first,” she said, suppressing a giggle.
My face was as red as an apple as I turned toward her for the first time.
“Uhm…uh,” was all I could say.
“Oh, you must be Jimmy’s mom,” Ms. Taylor said, “I’m his teacher at school, Jennifer Taylor.”
They all made their introductions as I stood there in embarrassed silence, my soggy diapers drooping heavily. I glanced up while they were talking just to steal a look at my teacher. She was wearing her long hair pulled up and behind which showed off her high cheekbones and gorgeous face. She wore a simple but snug white top, very low cut and I could easily see the curvaceous mounds of her generous breasts where they pushed together and formed a deep cleavage. I glimpsed an exposed section of tummy just above her skirt which came down just above her knees, showing off her shapely legs. Today, she was wearing a pair of white high heeled sandals with small little straps that went around her ankles. She always wore heels that were four or five inches high and impossible to ignore.
“Did you bring a change of diapers for your little Jimmy?” the saleslady asked pointedly.
Looking back down at me, my mom said yes and went out to the car to retrieve my diaper bag.
I was left standing there, fidgeting uncomfortably in front of these two women and wondering if my diapers were going to leak, I had peed so much. To my relief, my pink ruffled plastic panties were doing a good job of keeping it all in and the wetness could be clearly seen where my diapers clung to the panties.
“Jimmy, last time I saw you, you had a very sore bottom. I hope it’s feeling better today,” Ms. Taylor said sweetly. Her radiant smile was devastating, as always.
Before I could answer, the elder saleslady replied for me.
“I’m afraid that’s not very likely, he got himself into a little trouble this morning and earned himself another spanking from his mommy,” she said condescendingly.
“Jimmy! You’ve just become a naughty little boy recently,” Ms. Taylor said in surprise, “what did he do?”
“Turns out, this little sissy is also an avid masturbator. His mom caught him red-handed this morning.”
I’m not sure if it was possible to blush any redder than I already was, but if so, I just turned a deeper shade. My ears burned with shame at this humiliating discussion of my activities and at my expense. My mom returned shortly with my diaper bag.
“Excuse me,” she asked the saleslady, “but do you happen to have a place where I might change his diapers?”
“Oh certainly, come right over here,” she said, leading us to the area where changing tables were on display and that also happened to be in the middle of the store.
“Momm!” I pleaded in a whiney voice, “can’t we just wait?” I was desperate to avoid getting changed in front of Ms. Taylor.
Without responding directly, my mom stuffed my oversized pacifier into my mouth, effectively ending the discussion.
“You know, I’m going to need one of these so we might as well select one now that I can purchase,” she said, referring to the large assortment of changing tables available. She walked around eyeing them until she saw a low white table with a padded top, it’s surface covered with a shiny vinyl nursery print cover.
“This one will do quite nicely, don’t you think Jimmy?” she asked me in a taunting voice.
I could do little except suck the rubber pacifier in my mouth but my heart was racing at the prospect of getting changed right here in the middle of the store with all three women watching me. Ms. Taylor showed no signs of losing interest and she stood by eagerly as my mom pulled out the various items she needed from the bag. Sitting me down on the table, she pushed me back gently until I was on my back with my legs still off the edge. Lifting my dress and petticoats up, she reached under the elastic waistband of my plastic panties and began tugging them off the soaking wet diapers. I whimpered in embarrassment as she snaked them down my bare legs, pulling them over my knee socks and mary jane shoes. Next, she unpinned the sodden cloth and pulled it out from under me, placing it in an oversized ziploc bag before sealing it up. My little pee-wee shriveled even smaller at the unexpected attention and the saleslady stuck her finger down to tickle it.
“My, he certainly hasn’t developed much, has he?” she remarked disdainfully.
“No, I’m afraid his physical development has closely followed his childish behavior, neither of which has shown much maturity.”
A tear formed in my eye as she took some baby wipes and cleaned my damp bottom and crotch. Ms. Taylor had the bottle of baby lotion and she offered to apply it to my diaper area. My mom was only too happy to have her assistance and my teacher began slowing rubbing the lotion into my still pink cheeks.
“Well, looks like someone got his bottom soundly paddled this morning,” she said as she smiled down at me. I squirmed and blushed anew as she rubbed the lotion slowly across my still sore fanny. Her hands were very soft and despite all my efforts to the contrary, I found myself getting aroused. It didn’t help that as I looked over the multiple ruffled layers of my petticoats, I saw her immense breasts jiggling before me, barely contained within her tight top. Her hands moved from my bottom, tantalizingly slow up my crack, and then to my crotch, where I felt her slippery fingers caressing my tiny penis and balls. Ms. Taylor always had beautifully manicured nails and I watched as they encircled my little sex, rubbing the sweet smelling lotion in the most enticing manner. She had long, creamy fingers and they stroked me in the most sensual manner, sending electric waves of ecstasy through me. I swooned with pleasure as I gazed down her top, admiring her deep cleavage and the beautiful form of her tremendous boobs. She returned my lustful look through half closed eyes with her usual sweet smile. I grew harder by the second and I felt an orgasm quickly rising within me. My cheeks reddened and my body tensed in anticipation. I was seconds away from exploding and I shut my eyes tightly, sucking my pacifier for all it was worth. I shuddered as I tettered on the very brink of coming.
“There. That should do nicely,” she said abruptly, in her musical voice as she stepped back to allow my mom to powder me.
I gasped in frustration at the loss of what would have been the most intense orgasm of my life and my tiny wee wee flexed and twitched in unrequited pleasure. Breathing hard, I sucked my pacifier and bunched my fists as my mom began shaking scented baby powder all over me. A tear trickled down my cheek at the unfairness of it all.
Meanwhile, the saleslady held three thick, fluffy diapers in her hand patiently as she waited for my mom to finish. A cloud of baby powder rose up from the changing table as she took the diapers and slid them under my rump.
“Here we go Baby,” she told me lovingly, “a nice soft diaper to protect you with.”
I sniffled miserably at my fate while my mom tugged the thick but baby soft cloth around my hips and pulled it between my legs, snicking the large bunny pins through and locking them closed. After both sides were secured, she patted the bulging front of my diaper and smiled down at me.
“There you are. Time for your baby panties!” she exclaimed merrily.
I hated it when she said that, all the more since it was being said in front of these two women. As if things weren’t bad enough, a pair of young mothers entered the store and headed in our direction. Apparently wondering who was getting changed, they came over to investigate out of curiousity.
“Now, which plastic panties shall we wear today?” my mom asked, as if she were wearing them too. Of course, she didn’t really expect a response, and since I still had the pacifier in my mouth, I was in no position to reply anyway. Instead, she picked one of the pink nursery print panties from our basket and gathered the legs together in her hands. As the two ladies came up to see what was going on, my mom snaked the plastic panties up my skinny legs, wrestling them over the thick bulk of my diapers as she pulled them up and ran her fingers around the inside of the elastic waistband, ensuring that my diapers were completely covered. She did the same with the leg holes to be sure no stray bits of diaper were peeking through.
“Isn’t he a little old to still be wearing diapers?” one of the ladies asked.
“Not when he can’t keep his pants or bed dry for more than an hour,” my mom replied without hesitation.
They looked me over with strange looks and then moved on, occasionally looking over their shoulders at me. Still pouting, I sat up, only to have my mom push me back down again.
“Let me powder between your legs Honey,” she said as she shook the baby powder where my thighs rubbed against my plastic panties.
I looked up to see Ms. Taylor smiling down on me, her full, sensual lips making me want her all the more.
I stood up awkwardly, the fat bulk of my diapers forcing my legs outward in a babyish waddle. My mom took our items up to the counter and I waited impatiently as she made small talk with the saleslady.
Ms. Taylor was behind us in line with a baby toy in her hand and she looked at me as if still appraising me.
“Maybe I too, should get a playpen. I could put it in the classroom, and that way you’d be right at home, Jimmy,” she suggested.
I frowned but kept sucking on my pacifier. I was completely ashamed and now my idol had been a participant in my humiliation. She’d never look at me the same.
At last, my mom finished paying for all her items and I helped carry the playpen and changing table out to the car.
“Don’t forget your plastic panties Jimmy!” the saleslady called out to me as she stood in the doorway and held the full bag in her arms.
Several people in the parking lot looked at me and stared in wonder.
“Run along Jimmy, and fetch your panties,” my mom told me. She sent me off with a slap on my thickly diapered bottom.
“See you soon, Jimmy,” the sales lady told me with a wicked gleam in her eyes as she handed me the bag. That was one visit I wouldn’t be looking forward to.
“Bye bye Jimmy!” Ms. Taylor called out to me. As she turned away, I couldn’t help gazing longingly at her trim derriere, nicely displayed in her tight skirt.
When I returned to the car, my mom sat me in back and buckled me in again, replacing my pacifier with a large baby bottle of warm milk.
“Make sure you finish that before we get to our next stop,” she warned me.
Not wishing to get another spanking, I began sucking eagerly on the bottle, unconsciously adding to my sissyish appearance as people passed us by.
We pulled into the parking lot for a strip mall, in front of a shop that said ‘Candy’s Fashions’. With nervous haste, I finished off the last of the warm milk just as my mom came around to undo my belt buckle.
“Good boy,’ she said simply as she took the bottle and put it in my diaper bag. Taking my hand, she led me into the small shop which contained countless bolts of fabrics, along with a good selection of catalogs. A good looking woman in her mid-thirties came out from a backroom and greeted my mom warmly. They chatted briefly and then my mom stood aside to reveal me to her friend.
“And this is my sissy son that I told you about over the phone,” she said by way of introduction.
“Well young man,” she said looking me up and down, “from what I’ve been told, you’re a little boy who refuses to grow up.”
My mom had put my pacifier back in my mouth so all I could do was shake my head.
“But don’t you worry,” she said reassuringly, “we’re going to fix you right up!”
She pulled out a catalog of baby and little girl’s fashions, showing my mom different styles of dresses and outfits that she thought would be appropriate for a sissy still in diapers. They discussed a number of different items with my mom making sure each one would be sufficiently short in the hemline to leave my diapers fully exposed. The seamstress assured her she’d take care of that and after several designs had been selected, she showed my mom a sailor suit that could be made even more girlish than it already was with pink lace accents throughout.
“Excellent!” she agreed, “that will be perfect.”
The lady took several minutes and began thoroughly measuring me, getting my chest, waist, height, arms, everything necessary to create perfect fitting dresses that would be the envy of any little girl. On our way out, she called out to me:
“Oh Jimmy?” she said in a sing-song tone of voice. When I turned around she blew a kiss at me.
“Nice panties.”
I blushed red and hastened out of the store.

We pulled up a little while later in front of a salon. My mom took my empty bottle and led me inside where all the girls stopped what they were doing to openly stare at me. I blushed furiously as they gathered around me commenting on my outfit and appearance. They lifted up my dress hem and squeezed my diapers, oohing and aahing at how precious they thought I was. My mom explained that she wanted them to paint my nails and give me a little make-up, just enough to soften my features and make me look a little more girlish than I already was.
One of the prettier girls, a blonde named Barbie, volunteered to work on me. She sat me down and immediately began talking to me like I were a little child.
“Hello little boy,” she said very sweetly, “do you need your diapers changed before we start?”
“Nu-uh,” I replied, my face still a bright shade of red.
“Jimmy, it looks like you’re blushing. But don’t you worry. I’ll make you the prettiest little sissy in town,” she said with a giggle.
As she unscrewed a bottle of glossy pink nail polish, my eyes moved over her curvy form. She was wearing snug white jeans and a tight white halter top which showed off her perky breasts very sexily. Over that, she had on a long white lab coat but it didn’t obscure her beautiful body unless she turned around.
Placing cotton between my shaking fingers, she began methodically painting the glossy lacquer to my nails, taking great care not to go over the edges. As I watched, I felt the accumulation of all the milk my mom had made me drink starting to press insistently on my bladder. I tried to squirm in my seat but Barbie looked up at me annoyingly.
“Quite squirming Silly, you’ll make me mess up your nails.”
While Barbie worked, she focused on my nails, averting her eyes downwards which enabled me to stare uninhibited at her fabulous body. I watched the swell of her breasts rising and falling as she breathed and I was completely captivated. They were perky and proud, pushing against the thin fabric of her top insistently and I could clearly see the white demi-cup bra she was wearing underneath. My eyes gazed hungrily at the soft line of her cleavage as it disappeared into the low scoop neckline of her halter top. If I craned my neck, I could just glimpse the white lace where her bra cups were joined and my heart beat excitedly.
She must have sensed my straining to look down her top because she jerked her head up and stared at me hard with her piercing, beautiful green eyes. They penetrated me like knives and I felt extremely intimidated.
“Are you trying to look down my top?” she asked accusingly, as if she had read my mind.
“Oh no!” I insisted hastily, “no Ma’am!”
She furrowed her perfectly shaped brows and my heart skipped a beat as I grew fearful.
“You’d better not,” she snapped, “because I spank little sissies like you who think they can stare at me whenever they want.”
I shrank in my seat at her stern demeanor. Having a naturally submissive character, I was easily intimidated, especially by pretty girls who were so obviously superior to me.
“You see these?” she asked as she sat up straight and thrust her chest out proudly, “sissies like you will never get to touch them, so you might as well just put them out of your mind.”
I didn’t know what to say and she resumed her work on my nails, evidently terminating the discussion. Her words stung me but I had no reason to doubt them, coming from such stunning knockout like her. Still, I had nothing else to look at besides my babyish reflection in the mirror so I found myself watching her instead.
Even though her rebuke hurt me, I couldn’t help admiring her every feature. Her silky blonde hair cascaded gently over her shoulders, her cute button of a nose, and the dark glossy lipstick shimmered on her sensual lips.
I could tell she had a thin waist and it only accentuated her generous bustline. What I would give to reach over and fondle them, I mused, but I might just as well wish to catch the moon.
Barbie soon finished my nails and began applying a very light layer of foundation to my face. At first, I pulled back, not wanting to look anymore girlish than I already did.
“Do you need a spanking Sissy?” she said sharply.
“No Ma’am,” I replied in defeat.
“Then settle down. I’m only doing this for your own good.”
I wondered what good she was referring to and once again, she seemed to be reading my mind.
“Sissies like you need to be shown to the rest of the world as you truly are, simpering, effeminate, swishy little pansies,” she explained as she spread the make up over my face.
“Pucker up,” she ordered me curtly, as she unrolled a stick of Bonny Bell bubble gum pink lipstick and applied it generously to my pouting lips. First one coat, then a second, and then frustratingly, a third coat before she was satisfied. I was forced to cooperate or else I’d get a big pink stripe across my cheek.
Next, she brushed on a light application of pink blusher to my cheeks and an almost imperceptible amount of peach colored eye shadow.
“There, all set!” she said proudly.
“Aren’t you a little darling,” she said mockingly.
”Can I go now?” I asked meekly.
“Not yet Sissy. Let me get your mommy so you don’t cry,” she replied.
My mom came over and thanked Barbie profusely for her help, tipping her well for her efforts.
“Take a good look at yourself Jimmy,” my mom said as she faced me towards the full length wall mirror, “take a look at the big sissy you’ve become.”
I fought back tears as I gazed at my reflection, my bulging pink diapers easily visible beneath the layers of my ruffled party dress, my girlish knee socks and mary janes, the big pink bows in my pigtails, and lastly, the glossy pink lipstick and blush that shouted out to the world that I was nothing but a big sissy. Tears spilled down my cheeks and my shoulders began to shake with sobs.
“Awww…poor little baby,” Barbie said with mock concern, “I think he just wants his bottle.”
My mom, ever prepared, retrieved another full baby bottle of milk and handed it to the shapely beautician. She leaned over and while affording me another view of her cleavage, she coaxed the rubber nipple of the bottle between my quivering pink lips.
“There, there Baby,” she said soothingly, “suck your wittle ba-ba.”
The other girls giggled and gathered around us, a couple reaching down to squeeze the thick seat of my plastic pantied bottom. If I was looking for sympathy, I certainly wasn’t going to be getting any today.
“Jimmy, I want you to thank Barbie for making you up so prettily,” my mom instructed me.
Eyes downcast, I mumbled out barely audible thanks.
My mom’s arms swooped down and swatted the padded seat of my diapers, making me jump.
“No, that won’t do at all,” she said dissatisfied, “thank Barbie here for completing your sissy makeover.”
I swallowed hard as I paused in front of all the beauticians surrounding me and considered what another trip across my mom’s lap would feel like.
“Th-thank you,” I stumbled uncertainly.
My mom nudged me in the ribs indicating I wasn’t finished.
“Fo-for completing my sissy makeover,” I sobbed shamefully.
The girls all giggled at my recital and Barbie pushed the bottle back into my mouth.
“Anytime Sissykins. Come on back when you get potty trained,” she remarked derisively.
Amidst more giggles and laughter, we left the shop and my mom put me in the backseat again. By now, my bladder was bursting with all the milk I had been forced to drink and the bumps we drove over were torture. The last thing I wanted to do was to wet my diapers to the degree where they’d need changing-my mom would probably do it in the most public place possible. So I just thought I’d just try and relieve a little of the pressure by letting out a tiny trickle.
Relaxing ever so slightly, I felt a small stream of pee flow into my diaper. But all of a sudden, the car hit another bump and I lost what little control I had. Before I could stop it, I quickly soaked the front of my diaper and my bladder hurt when I tried to hold back the rest. With depressing certainty, I realized that by now, there would be no concealing my wetness if mom should check me so I went ahead and just let it flow.
For the second time today, I flooded my diapers, squirming in my seat as the warm pee drenched the front and then began seeping down between my legs. As I sat there, getting used to the warm wetness surrounding me, I felt the pee soaking into my seat, clinging miserably to my cheeks.

Another bottle of milk later, we pulled up in front of my aunt’s house. Once again, the empty bottle was replaced with my pacifier and I was taken inside. My heavy diapers sagged under the weight and I tried to hold them in place without my mom noticing.
“Hello Jimmy!” my aunt greeted me enthusiastically. She came forward and hugged me tightly, mashing my face against her big breasts which I didn’t mind too much. For a moment, I remembered last night on her bed while I suckled from her boobs and had that wonderful orgasm. I wondered if she was still wearing the same sexy bra she had on then.
“You’re just in time, come on inside,” she urged us as she lead us through the door.
I wondered what she was referring to when I waddled in and saw her sewing machine out and various pieces of cloth laying about. At the end of her coffee table was what looked like a short stack of rhumba panties, silky and lace covered in pinks and whites.
“Hey Sis,” she said to my mom, “just look at these scrumptious creations I’ve finished.”
My mom’s face lit up as she picked up each pair of ruffled panties and examined them.
“Perfect. Just perfect,” she exclaimed, clearly impressed.
“Let’s try them on him!” aunt Susie suggested eagerly.
Picking one at random, my mom held up a pink pair of silky panties, with three rows of sassy ruffles adorning the backside. Gathering the leg holes in her hands, she held them down for me to step into. I knew better than to argue with her and bracing myself against her shoulders, I stepped carefully into the leg holes, trying not snag them with my mary janes. My mom pulled them up my legs but she paused when she got them mid-thigh.
“Jimmy? Have you wet your diapers, again?” she asked accusingly.
My lips quivered in shame.
“Y-yes Mommy,” I mumbled.
“Well you’re just going to have wear these for now, because I don’t have any fresh diapers for you until we get home,” she said sternly.
With that, she continued hitching the rhumba panties up and over my bulging diapers and plastic panties while I looked away in embarrassment.
“They’re just darling!” she announced, “absolutely darling!”
“Thank you,” aunt Susie replied, obviously pleased with herself, “don’t you just LOVE the cute ruffles I put around the leg holes? They give him such a dainty look.”
“Oh definately! They really dress up his outfit,” she concurred.
“Try these,” she offered, holding forth a pair of white and baby blue lace covered panties, “I thought these would go great with a little sailor suit.”
“You must have been reading my mind!” my mom burst out, “we’re getting a wonderful sailor suit made up for him right now.”
I pouted helplessly as she pulled down the first pair of rhumba panties and snaked the other up in its place. The panties fit snugly and they had the added effect of holding the wet cloth of my diapers right up against my skin. I felt so babyish and frustrated I wanted to cry.
“How CUTE!” she commented happily.
Lastly, she had me put on a pair of frilly pink panties in a sparkly material with white lace accenting it.
“These look like dance panties, don’t they?” my aunt asked.
“Yes, it makes me want to enter him into a dance class,” my mom chuckled.
“Why not teach him some steps right here? Just for our own amusement?” aunt Susie asked.
“Why not?” my mom quickly agreed, “why let such fabulous panties go to waste?”
“Jimmy, I want you to do a twirl for us. Hold your arms up and your hands like this,” she instructed me, showing me how she wanted me to hold my hands up in a sissyish pose.
I twirled around but without too much enthusiasm to which my mom regarded me sternly.
“Jimmy? Do I need to re-warm that bottom of yours?” she asked. To emphasis her threat, she reached into the diaper bag and produced my paddle.
“Uh-um!” I whimpered through my pacifier as I shook my head vigorously.
“Then twirl around like you mean it!” she ordered me.
I twirled around on my tip toes, holding my hands out and up like a sissy ballerina. The hem of my dress lifted up obligingly, exposing my frilly rhumba panties gaily.
They both clapped eagerly at my performance until a knock at the door interrupted them.
“Oh!” Aunt Susie remarked, “that’s probably the babysitter I wanted you to meet,” she told my mom. “She’s a friend of a friend, who comes highly recommended and can keep an eye on Jimmy when you’re away.”
“Great! That was very kind of you to find someone on such short notice.”
“Not at all,” my aunt answered as she walked to the door.
“Her only stipulation was that she be able to discipline Jimmy however she sees fit,” she said from over her shoulder.
“Sounds like my kind of babysitter,” my mom agreed.
My aunt opened up the door and let a tall, but young female inside, ushering her into the living room where we were waiting.
Oh no!! My jaw dropped open in panic as I recognized who it was.
It was Melissa from my school!


Jimmy’s Day at School

“Jimmy! You’re going to be late for school!” my mom called from out in the hallway.
I rolled over in my bed sleepily, before swinging my feet out to get up. My thick, nighttime diapers were soaked as usual but the snug plastic pants kept my sheets dry. I had been wetting the bed ever since I was six, when my dad left us and my mom had decided that diapers were the best solution to my nightly problem. My mom, never one to take chances, had also replaced the mattress cover with a vinyl waterproof sheet years ago and it crinkled loudly as I got up. I was dressed only in my diapers and nightshirt, the latter of which was more of a nighty, than a pajama top. When my mom first started diapering me for bed, she initially consented to allowing me to continue wearing my pajama bottoms but after several weeks, I had managed to rip the back seams out in every one because of the thickness of the diapers. Eventually, she dispensed with them entirely and threw the ruined pajama bottoms in the trash. As time went on, she replaced my tops more and more with decidedly feminine wear, telling me she didn’t want to waste money on pajama bottoms that would just be thrown out.
Today’s top was a short hemmed, puff sleeved frock, with a flower print that I prayed no one would ever see me in. Besides the fact that it looked like it belonged to a little girl, it did nothing to hide my embarrassing diapers which remained humiliatingly exposed.
Waddling out into the dining room, I sat down and began eating the breakfast that my mom had prepared for me. I was thirteen years old and attending a private school but my mom often treated me like I was still four. Instead of serving my juice, she always gave me a tall glass of milk in the morning and rather than call me by my given name, Jim, she referred to me as ‘Jimmy‘, much to my chagrin.
As I ate my cereal, I felt a stream of warm pee further saturate my already soaked diaper, seeping down between my legs and collecting in the soggy cloth under my rump. While it’s true that perhaps I didn’t make enough of an effort to keep my diapers dry as I should have, I reasoned that since they were already wet, I might as well just use them anyway. But despite the humiliation I felt wearing them, I sure was glad I had on a snug pair of plastic pants.
After breakfast, I met my mom back in my bedroom where she had my changing pad laid out, along with a fresh diaper. Unfortunately, my mom had gotten tired of my half-hearted attempts to control my daytime accidents and she finally settled on diapers and plastic pants for that problem as well. I probably wore the baggiest pants at school but so far as I knew, no one had caught on yet about my “situation.” My mom said I was just lazy, and I could stop wetting my pants whenever I wanted, but I always hotly denied it.
Sometimes, when I was frightened suddenly, or laughed too hard, I’d let out a trickle of pee before I could stop it. I hated wearing diapers but my mom was convinced that they were the only solution for my problem. I was helpless to stop her once her mind was made up, and I knew only too well that she would show no hesitation in pulling them down and putting me over her knee for a good hard spanking if I were to put up too much of a fuss.
This morning, I was anxious to get my wet and sagging diapers changed so I sat down without argument while she busied herself pulling down my clinging waterproof pants. With expert efficiency, which came from doing this day after day, she soon had my diapers off and was wiping my damp bottom with baby wipes. I said nothing as she scooped up some diaper rash cream and smeared it across my bottom until it was coated with a thick, white layer of the goop. She slid my fresh diaper under me and powdered my front area generously, perhaps a little too generously, I thought nervously, since I feared that someone might smell it on me later at school. I had a reputation among some of the kids that I was a sissy and the last thing I needed was for them to smell baby powder on me.
“That’s enough!” I protested in a whiny voice but my mom only stopped briefly, before wordlessly shaking some more on me.
“Someone will smell it on me!” I complained vehemently.
“Hush Dear,” my mom said, blithely dismissing me. She pulled up the soft but thick cloth and held each corner firmly as she pinned them securely with two big bunny shaped pins.
Gathering the leg holes of some plastic pants, she began sliding them up my skinny legs but I realized to my shock that they weren’t the usual white ones. Instead, they were a pink nursery print with small frills around the leg openings that I had never seen before.
“Hey! What are you doing? Where are my normal pants?” I asked in a panic.
My mom was no pushover, and despite my frantic kicking, she easily slid them up my legs and over the bulging cotton cloth of my diapers.
“I’m sorry Honey, but all your other ones are in the laundry. This is all you’ve got for now,” she said sympathetically.
“Bu-bu…Then I’ll just wear what I had on last night,” I cried as I stared down at the babyish plastic pants covering my diapers. The infantile bunnies and clowns decorating the vinyl seemed to shout out baby, loud and clear.
“Oh Jimmy…honestly,” she said as she began putting away the rest of the supplies, “you can’t wear the others because they’re wet and need to be washed. And I’m not going to send you to school with soiled plastic panties. What kind of mother would that make me?”
I hated when she called them panties, it sounded so sissyish.
“They’re pants not panties,” I protested bitterly.
“Yes Dear,” she replied tiredly. She always said ‘yes Dear’ when she didn’t feel like arguing with me but she never changed her mind. I think my mom thought I was a sissy too but she didn’t actually come out and say so.
I hurried to get dressed and soon we were on our way to school. It seemed like my jeans were tighter than usual but no amount of trying to compress my padded middle would change my appearance. It was frustrating but I just hoped that no one would notice.
As usual, I had my Scooby–Doo lunchbox with me which I felt very self conscious about it but my mom refused to get me another. I had gotten bullied at school but she could never see why it was an issue for me.
But my main fear today was that one of the older kids would decide to pull my pants down as a prank, as they had done to my friend Johnny last week. That would be mortifying. I shuddered as I thought of the humiliation I would feel if people were to see not just my diapers, but the babyish nursery print plastic pants I had on.
“Mom?” I started anxiously, “I was wondering…do you think I could start wearing training pants to school?”
“Training pants?” she said incredulously, like it was the silliest thing in the world, “I don’t think so Jimmy. You’d just wet through them if we were to do that.”
“But I’d really try hard to keep them dry!” I insisted.
“No Dear,” she said simply, which clearly indicated she thought such a thing was ridiculous, “No, I think diapers and plastic panties are better suited for you. Maybe someday you can graduate to training panties but for now I think we’ll just stick with the diapers.”
Her tone indicated the discussion was over and I sulked as I sat back in my seat.
Soon, we reached my school and she let me out, giving me a kiss on the cheek before saying goodbye.
“Bye-bye Jimmy!” she called out, much louder than I would have liked. A couple of girls nearby giggled and began whispering about me as I turned and rushed inside.
I walked into my classroom, praying as usual, that no one would notice the thick bulkiness of my diapers pushing against my jeans. Sitting down at my desk, I watched as Ms. Taylor, our teacher came in.
She was a goddess as far as I was concerned and I was totally in love with her. She was in her mid-twenties, drop dead gorgeous, tall and slim, with a generous bustline that I estimated to be double D in size. She had a habit of wearing provocative outfits and today was no exception. In keeping with the warm spring weather, she had chosen a light colored dress of a breezy material that went about mid-thigh and showed off her smooth, sexy legs, particularly when she sat down. In addition, her big, curvy breasts were tightly encased in a scoop necked, low cut dress that made it impossible to concentrate on my schoolwork. I found myself staring at her unbelievable figure as she stood before the class and brought the class to order.
While she talked, she made a point of walking slowly around the room and I admired the practiced ease in which she moved in her stiletto high heels. I was oblivious to what she was saying but I felt my wiener stirring within my diaper as I stared at her incredible profile. Her big bust was further accentuated by her flat tummy but my eyes were riveted to the long line of cleavage that disappeared into the low cut U of her dress. I blushed at the thought of kissing the exposed soft skin of her breasts that were literally bursting out of her dress. I thought I caught sight of a flash of lace from the cups of her bra and my heart beat with lustful desire.
I had tried desperately to be the teacher’s pet and had made a point of ingratiating myself with her at every opportunity. From time to time, she graced me with her devastating smile which only fueled my fantasies and made me think she felt the same way about me. I was certain that I could do no wrong in her eyes and I felt a confidence that was perhaps misplaced. I was to find out just how misplaced it was later…

When I was on first break, I unexpectedly ran into Melissa, one of the tough girls in school. She was much taller than me and I knew that if push came to shove, she could easily beat me in a fight. Especially since I was small, slight of build, and by most standards, frail in body. I found her intimidating and I feared her taunts, especially when she was in the company of her friends, Michelle and Tara.
I was heading back to class when the three suddenly surrounded me and blocked my path.
“Where ya goin’ Sissy?” Melissa asked in a threatening tone of voice.
I bit my lip nervously and tried unsuccessfully to prevent a trickle of pee from escaping into my diaper.
“Back to class,” I said in my high pitched voice which made me sound like a scared mouse. I tried to move past but Tara put her arm in my way. She was much taller than me and her substantial breasts were at my eye level, blocking my view of anything else.
“Not so fast Sissy-boy,” she snarled, “we’re going to have a little fun.”
“Wha-what do you mean?” I squeaked pathetically.
Melissa suddenly reached down and squeezed my bottom, instantly feeling the thick padding under my jeans.
“Are you wearing diapers?” she asked bluntly.
I tried to bolt between them but Tara blocked my path.
“Oh no you don’t, Sissy-boy. You haven’t answered her question,” she said insistently.
“That’s right Baby, when a woman asks you a question, you answer her!” Michelle added with venom.
In my panicked state, I felt another stream of warm pee seep into my already damp diaper.
Without another word, Melissa suddenly reached around and unsnapped my pant’s button. I struggled but the other two held me firmly as my tormentor yanked my jeans down to my ankles.
“Oh—My–God!” Tara said in disbelief.
“What a sissy!!” Michelle cried.
“Just as I always thought,” Melissa said with a smug look, “this little boy still needs his diapers.”
I blushed a hot, deep shade of red as they stared openly at my humiliating pink plastic panties.
Suddenly, without warning, Melissa giggled and pulled the fire alarm. The blaring sound of the siren filled the hall and everyone piled out of the classrooms. As the three girls bolted out of the hall, I tried to jerk my pants back up in an attempt to hide my embarrassing diapers before anyone saw me. I only managed to half stumble, half jump, out onto the playground when the teachers came out.

Later, as everyone filed back into class, I was filled with apprehension over the incident of the fire alarm. I was too timid to break the rules or cause trouble but I happened to be one of the closest students to the alarm, and the last seen running out of the school. As I took my seat, I opened up my textbook to try and look as innocent as possible.
“Jim?” Ms. Taylor asked suddenly. Her voice sounded very serious and it matched the look on her beautiful face.
“Y-yes Ma’am?” I quaked uncertainly.
“Please come up to my desk,” she said sternly.
Reluctantly, I slowly rose from my desk and I saw her reaching into her own to get something out. My heart began pounding in my chest as I saw her take a wooden paddle from the drawer and set it down on top of her desk. Surely she couldn’t be intending to use that on me? I was her favorite student, wasn’t I? Didn’t I do everything I was told to, volunteering for extra credit and being the first to raise my hand, in hopes of being rewarded with one of her heart stopping smiles?
As I slowly walked up to the front, my knees felt weak and my throat went suddenly dry. Butterflies swirled in my stomach as I imagined what it would be like to get paddled over my pretty teacher’s lap.
“Ye-yes?” I asked fearfully, looking from her to the paddle and then back to her again.
“I’ve been told that you were the one who pulled the fire alarm today at first break,” she said evenly.
I gulped nervously as I realized this was my only chance to prevent being spanked. I had to think quick!
“Bu-but M-Melissa’s the one that did it!” I blurted out rashly, pointing her out in the third row back.
“Jim, I heard it from several of the kids, not just her, I’m afraid I’m going to have to give you a spanking,” she said with finality.
“Wha-what?” I stammered, trying to think of a way out of this. I just realized that I was still wearing the nursery print plastic pants that my mom had dressed me in and soon everyone in the class, including my beautiful teacher, would see them. I backed away nervously but she quickly reached over and snatched my wrist. I tried to struggle out of her grip but she held me like a vice and my efforts showed just what a weakling I really was. I couldn’t help but notice her two big breasts jiggling enticingly as she held me with one hand and with the other, unzipped my fly. I let out a small cry of despair as she unsnapped my pants and tugged them down and over the thick diaper I had on underneath. I blushed crimson and felt a stream of warm pee leak into the soft folds I was encased in.
The classroom of kids let out a collective gasp as they took in the babyish looking diaper and pink plastic nursery pants I was now openly displaying. My ears filled with the sounds of giggling all around me and I could see Ms. Taylor was clearly shocked. She recovered quickly however and she stared me in the eye with firm determination.
“Jim, are you wet?” she asked, eyeing the colorful nursery characters decorating the panties.
I felt the blood rushing all the way from my cheeks to the tips of my ears.
A tear formed in my eye as I slowly nodded yes. I had never been so humiliated in my entire life. I thought that maybe if I admitted to being wet that she would spare me the additional humiliation of a spanking. After all, wasn’t this punishment enough? But the look on her face indicated she had every intention of spanking me, wet diapers or not.
In response, she pulled the hem of her dress up to the top of her thighs, probably so that the wet diaper wouldn’t stain her dress. Her smooth, silky thighs were perfect in every way and I gazed at them admiringly, even as I anxiously contemplated the coming spanking. She reached forward to pull my waterproof panties down and her breasts were pushed together, creating a curvy Y of two joining cleavages. It was breathtaking to behold but I became panicky as she started to snake the panties off my diaper and down my legs. I shifted nervously and tried to stop her but she simply pushed my hands away and continued until they were gathered around my ankles. I saw her eyes staring at the yellowish wet spot in the front of my diaper and I blushed an even deeper shade of red, if that were possible. She looked me back in the eye with a look of disappointment and shook her head.
I was so ashamed. Here, the idol of my life was now fully aware that I needed to wear diapers and plastic pants like a baby to keep my pants dry. All my efforts were for naught! And now she was going to spank me like a naughty little boy, in front of the entire class!
All too suddenly, she pulled me over her lap and began unpinning the thick folds of my diapers.
“No Ms. Taylor! Please! I didn’t do it!” I pleaded desperately, “It wasn’t me!”
“I don’t like little boys who lie to me,” she said as she pulled the cloth back and exposed my fanny to the rest of the eagerly attentive class, “but my paddle usually brings out the honesty in them.”
I began whimpering and crocodile tears filled my eyes as I stared down at her curved calves and the small straps that held her high heels on.
“Please don’t spank me! Please? Please?!” I begged her pathetically. I had never been spanked in public before and tears of shame streamed down my face.
The rest of the class craned their heads forward for a better view as they waited eagerly to watch my punishment.
Looking up, I saw the face of Kelly Kendall smiling back at me. She was the cutest girl in our class and head of the cheerleading team. She appeared very amused with my situation and if I was looking for sympathy, there was none coming from her.
Before I could dwell on that however, Ms. Taylor shocked me with the first, crisp slap of the paddle on my upraised bottom.
I yelped in pain and the paddle came down again, even harder. Maybe I really am just a sissy because I immediately burst into real tears and began crying like a baby.
Ms. Taylor delivered the spanking with fierce determination, swatting my tender cheeks with harsh, angry slaps. I gasped in pain and kicked my feet wildly, no longer concerned about maintaining any pretence of dignity.
I wailed loudly and beat my fists on the ground in futile impotence. The hard wooden paddle left its searing impression on my bottom again and again and I knew it was a bright shade of red, matching the flushed color of my face. I sobbed and wailed but Ms. Taylor never eased the pace or the severity of her spanking.
“Are you ready to be a good boy?” she snapped at me harshly.
“Ye-yes-yes!” I cried between sobs. My face was wet with tears and my nose was runny but I cried like a baby.
I bawled and bawled, my dignity forgotten as I howled over her lap, gasping for air between sobs.
“That’s better,” she said as set the paddle down on the desk with a clatter. My bottom was blazing and hot as she pulled my diapers up snugly and re-pinned them. Helping me up, I rose to my feet shakily, my crying still unabated. When it became apparent that she wasn’t going to pull up my plastic pants, I reached down and hurriedly yanked them up which only sealed in worse the fire crackling on my punished fanny. When I reached down to do the same with my trousers, she put the toe of her high heeled sandals over the middle of them, holding them down on the floor.
“No, those can stay down for awhile,” she said firmly, “I want you to put your nose in the corner and think about just what you’ve done.”
I sobbed with embarrassment and shuffled over to the corner by the blackboard, knowing my colorful plastic pants were now on full display for everyone to see. It would be years, if ever, before I lived this day down.
Behind me, barely stifled giggles rang humiliatingly in my ears.

Sometime later, Ms. Taylor let me pull up my pants and gave me a note to take to the school nurse so I could get my diapers changed. I left the classroom and dragged my feet down the hall, rubbing my sore bottom as I went. It still stung painfully and I wondered how my mom would react when she saw it tonight. I hoped she wouldn’t spank me too for having misbehaved at school. That would just be too much. My poor fanny wouldn’t be able to take it!
I walked down the hall and entered the door to Ms. Jones’ office reluctantly, hoping against all hope that she’d be away on some business. My heart sank when I saw the pretty brunette nurse bandaging a girl’s arm, about the same age as me. She looked up from her work and flashed a dazzling smile at me, apparently recognizing me from around school.
“Hello, Jimmy,” she greeted me cheerfully, “I’ll be right with you.”
I mumbled something incoherent and hoped she’d send the other girl on her way before she attended to me.
As if to contradict what I was thinking, she set the girl’s arm down and stood up saying:
“Now, what can I do for you, young man?”
Hesitantly, I handed her the note from Ms. Taylor as I tried to minimize it’s importance.
“It’s really nothing,” I said as I watched her unfold the note and read it with a look of surprise on her face. Her gaze immediately dropped down to my pants, and the bulk I was doing my best to hide.
“I didn’t know you wore diapers, Jimmy,” she said as she reached down to unbutton my pants. I tried to pull away but she succeeded in unzipping and lowering them, exposing my nursery print plastic panties.
“Well, aren’t these cute!” she exclaimed as she beheld my embarrassing diapers. The other girl stared at me with disdain and I blushed furiously.
“Let’s see, I don’t know if I have any plastic panties but I’m sure I can find some fresh diapers for you,” Ms. Jones offered eagerly.
“Jenny, I think we’re all done with you, you can go back to class now,” she instructed the girl watching me.
“Thanks Ms. Jones,” she replied as she stood up and walked out past me. She took one more look up and down me as if committing my image to memory before leaving.
The nurse had me sit down while she poked around the room and found the items she needed, baby powder, diaper rash cream, and at last, several thick cloth diapers.
“I don’t normally get boys your age still wearing diapers but you’re in luck today, these should fit you just fine,” she told me with a big smile.
I groaned inwardly at her statement thinking that today had been anything but lucky for me. As she pulled down my clinging plastic pants, she took them off my feet and wiped the damp insides with a baby wipe.
“We’ll just re-use these since I don’t have any in your size,” she explained as she set the nursery print panties aside, “besides that, you look cute as a button in them!”
Unpinning my diapers, she removed the sodden cloth and set it down next to me. “I’ll put this in a bag and you can pick it up after school. Okay, Honey?”
“Uh-huh,” I mumbled ashamedly, keeping my eyes downcast.
She wiped my crotch and the inside of my legs gently and I couldn’t help but stare at her perky breasts, pushing against her tight white top. She grasped my ankles and raising them over my head, she began wiping my still pink and red bottom.
“My my…looks like someone got his little bottom spanked today,” she said observantly, “were you a naughty little boy in class?”
“No!” I insisted, “Melissa told Ms. Taylor I pulled the fire alarm-but I didn’t!”
“Mm-hm,” she said as she lowered my legs. Obviously, she didn’t believe me for a minute. She took the three diapers, arranged them in a stack, and began sliding them under my sensitive rump.
“Um…do you think I could just wear one, Ms. Jones?” I asked tentatively. I was used to wearing just two and I was sure that three would be obvious under my pants.
“I don’t think so Jimmy, you look like a heavy wetter to me. Better that you have the protection you need,” she said as she took a handful of diaper rash cream and began applying it to my still stinging fanny. She was sprinkling baby powder on my tiny penis when the school principal suddenly walked in, unannounced.
It was Ms. Stern, an appropriately named disciplinarian who had resided over the spankings of countless students. She was in her mid-thirties but still quite striking in her high heels and professional attire. She wore her dark hair in a severe bun that seemed to make her fierce demeanor, even more intimidating.
She stared down at me harshly, as if she intended to put me over her lap just for being there. I quaked with fear even as I blushed anew at her unexpected appearance.
“Well, it’s not too often I see you changing diapers in here,” she said mildly surprised.
“You’re quite right Helen, it seems this little boy wet his only pair,” Ms. Jones said with a chuckle. She pulled up the thick, bulky cloth and put a pin through either side. I could barely close my legs together, it was so fat and bulky.
“It’s too big!” I complained bitterly.
“Don’t worry Honey, I’m sure your plastic panties will fit over them just fine,” Ms. Jones assured me.
I was about to complain further but the look on Ms. Stern’s face warned against it.
Taking my nursery print panties, she gathered the leg openings together and slid them up my legs, the plastic crinkling as it was pulled up my thighs.
“Up-sa-daisy,” she said cheerfully as she yanked them up and around my fat, bulky diaper. She ran her delicate fingers around the waistband to make sure all the cloth was contained and then as I stood up, she swatted my thickly padded bottom playfully.
“There you go, Jimmy. All diapered and ready to go!”
I winced and did my best to pull my jeans up and over the diaper but it was just too fat. No amount of effort was going to get my pants to cover them, never mind, allow me to zip them up.
“See! It’s too big!” I whined petulantly.
Both women looked at me unsympathetically. Ms. Stern just shook her head and the nurse put her hands on her hips, making no effort to alleviate my predicament.
“I know!” she said suddenly, “I think I’ve got a pair of shorts you can borrow. They were left by an older student last week.”
I felt a small sense of relief but I was also sure that nothing short of a poncho was going to be able to hide the obvious bulk of the diapers I was presently wearing. Ms. Jones dug around in a drawer and then pulled out some silky gym shorts that were pink with white trim.
“Here we are!” she said brightly, “these should fit perfectly!”
“I can’t wear those!” I cried, “they’re for girls!”
“Now Jimmy, I know these aren’t exactly what you had in mind, but I think it’s best that you give it a try. It’s all I have. And your alternative is to go without any pants at all. You don’t want that, do you?”
I pouted and felt tears in my eyes as I shook my head no.
“That’s a good boy. Now let me help you put these on-”
“-I can do it myself!” I interrupted defiantly, angry and resentful.
“Well!..Fine then,” she said rather insulted, “I can see now how you got your spanking today.”
“Sounds to me like you need a little attitude adjustment, young man,” Ms. Stern said ominously.
I bit my lip nervously as I hiked the shorts up and over my diapers. They were stretchy and snug enough that they left absolutely no doubt as to what I was wearing beneath. Indeed, they could almost pass for rhumba panties if they had had ruffles across the seat. I sniffled with embarrassment as Ms. Jones folded my jeans into a neat package and set them next to the bag that had my wet diaper in it.
“Am I done now?” I said, as a tear trickled down my cheek.
“Yes Jimmy, you can go back to class now,” she told me.
Without another word, I shuffled back down the hall, waddling because of the thick bulk between my legs. I stood outside my classroom door for ten minutes before I had the courage to open it and step inside. Everyone’s eyes, including Ms. Taylor’s, immediately looked up at me and stared openly as I tried to walk normally to my seat. All of the girls were giggling and began talking amongst themselves until Ms. Taylor shushed them and brought the class back to attention.
I was ready to die of embarrassment.

At the next break, I was walking down the hall, trying desperately to be inconspicuous but I felt the stares of everyone around me, looking at me and in particular, the silky pink shorts that were clinging to my thick diaper. In quieter moments, the unmistakable crinkle-swish of my plastic pants could be plainly heard, bringing further ridicule upon me.
A group of girls called me a diaper sissy and some others asked if I needed changing.
Since I was keeping my eyes downcast in embarrassment, I didn’t notice when Tara suddenly appeared and took hold of my arm. With her strong grip, she ushered me into the girl’s bathroom where Melissa and Michelle were waiting. My nemesis was dragging on a cigarette as she looked me up and down contemptuously.
“Well Diaperboy,” she said with a sneer, “so you thought you’d try and blame the fire alarm on me, huh?”
I looked around in panic but the tall high school girls had a firm grip on my skinny arms.
“Let go of me!” I squealed imperiously.
Tara yanked my pink gym shorts down revealing my nursery plastic pants again.
“You really look more natural with your diapers exposed, Sissy boy,” Michelle said condescendingly.
I stamped my feet in frustration which only made me look more like the sissy weakling they were calling me.
Melissa was wearing a short black skirt and a snug striped top that hugged her generous bosom. I watched in amazement as she unzipped the back of her skirt and began sliding it down, revealing a pair of high cut black lace panties. She stepped out of the skirt with her high heel pumps and taking a tall trashcan, she upended it, placing it upside down in the middle of the bathroom.
“Today we’re going to have a little fun with you baby boy,” she said in a threatening tone of voice. I was at loss to understand what was going on until I saw her reach into her gym bag and produce a big rubber dildo, that was securely attached to a series of straps, like a harness. As she stepped into the device, I watched breathlessly as she pulled it up her long thighs and began cinching up the straps. When she was done, the big dildo stuck out boldly, it’s eight inches of fat rubber contrasting with Melissa’s very feminine body.
I wasn’t sure what she had in mind but I knew I didn’t like the look of it. I struggled mightily against my captors but they easily forced me down on my knees.
“You might as well get used to this Sissy boy,” Melissa said with a gleam in her eyes, “’cause this is where you belong-on your knees, sucking cock.”
The others laughed heartily as Melissa guided the big dildo toward my mouth.
“No! no-please!” I pleaded, “I don’t wanna-”
She cut short my frantic pleas by stuffing the fat rubber cock past my lips, throttling me with it as I choked, unprepared for the massive penis being thrust into my mouth.
“Suck it sissy,” she warned, “suck it good.”
Obediently, I slobbered and slurped on the dildo, keenly aware of the humiliating position I was in. I blushed hot red as my cheeks were stretched wide to accommodate the thick cock, and Melissa guided my head up and down, moaning in mock ecstasy.
“That’s it, show everyone what a good little cocksucker you are,” she said admiringly.
I whimpered meakly, as my head bobbed up and down on the dildo and I was so embarrassed, tears of shame trickled down my cheeks.
Melissa pulled it out of my mouth and I gasped for air as I stared at the saliva covered cock.
“Kiss it Sissy,” she ordered me.
Doing as she told me, I gave the wet bulbous head a big kiss and she pushed it past my lips again. I found myself deep throating it as she slid it in and out of my mouth, guiding my rhythm with her hands.
Just as my jaws were starting to get sore, she pulled it out.
“Okay Baby boy, enough fun for you. Now it’s time for me to show what you can look forward to, the rest of your life.”
The other girls picked me up off my knees and Tara began yanking my plastic pants down.
“Don’t you worry, Sissykins,” she said with mock concern, “I won’t harm your pretty little plastic panties.”
I squirmed and fidgeted while they unpinned my diapers and bent me over the trash can. Michelle moved around the front to hold me in place and keep my bare bottom exposed in back.
“My, my,” Melissa said as she gazed down at my pink fanny, “Ms. Taylor certainly knows how to use a paddle doesn’t she?”
“Let go of me!” I squealed pitifully, “let go of me!!”
“Spread your legs Sissy,” she ordered me sternly. Using the toe of her high heels, she kicked my feet outwards, making me spread my legs apart as I remained bent over at the waist.
“Please Melissa, I’ll do anything you want,” I implored her, “please, please let me go!!”
She ignored me as she dipped the big head of the strap-on into a jar of vasoline, coating it liberally. Then she brought it up behind me, rubbing the head teasingly against my puckering anus.
“This is what all big sissies need, Diaper boy,” she said, stroking the head against my hole.
“Nooo!” I wailed, “I want my mommy!”
With an abrupt move, she slapped my right butt cheek painfully hard, leaving a stinging impression of her hand on the already pink skin. I yelped in pain and felt as she pulled my cheeks apart and began pushing firmly and determinedly with the strap-on. Instinctively, I tried to move forward to escape the fat rubber invader but the trash can and Michelle kept me in place.
“It’s too biiigg!!” I cried as Melissa wiggled it around, pushing harder and harder against my sphincter. She slapped my butt cheek again and kicked my feet out farther, forcing me to keep my balance by grasping the sides of the can.
“Oww!” I wailed in a girlish voice, smarting from the sting on my bottom. This sensation was quickly replaced with the feeling of the dildo sliding in past my opening.
“OHHH!!” I moaned as I felt the thick cock filling me up. Michelle and Tara smiled at me satisfied as they watched the dildo get buried in my backside. My mouth was open and I lay there gasping as Melissa waited long enough to allow me to get accustomed to it. Then, she began slowly pumping me, in and out. I moaned like a little girl, no longer concerned about trying to act like a big boy. Slowly, and with great deliberation, she pumped me from behind, forcing every inch of the big dildo into my pouting bottom. I sighed every time it eased out and moaned when she’d push it back in. Taking her time, she humped me with long, patient strokes, grasping my hips and forcing the dildo in as far as it would go. She’d hold it there while I squealed and squirmed, trying desperately to escape the fat rubber invader but to no avail. Melissa was going to make sure that I got every bit that I deserved and she was in no hurry to ease my punishment.
Off to my right, I could see our reflections in the mirror. Me, the sobbing sissy bent over and getting humped relentlessly and Melissa, the tall senior, her beautiful face a mask of determination and satisfaction. Every time she thrust forward, her breasts would heave within the confines of her top, jiggling and swaying in an erotic display. She looked so powerful with her firm, long legs, as she stood confidently in her high heels, a vision of strength and superiority as she plunged the strap-on into my waiting, virgin bottom. Her brows were furrowed on her forehead from her efforts and she grasped my hips with hands of steel.
Even though by now, the slippery dildo was sliding in and out with ease, my hole was becoming sore and I whimpered like a girl. I gave up struggling against my tormentors and just lay there, taking my punishment submissively.
At long last, she eased the dildo out and began wiping it clean with some wet wipes she had in her bag.
I was exhausted and lay panting as Michelle pulled the back of my diapers up and re-pinned them. She pulled my plastic pants up and hitched them over the bulk of my diapers but left my shorts in place.
“Maybe that will teach you a lesson next time you try and squeal on me,” Melissa warned me as she caught her breath.
“Yes Ma’am,” I whispered in defeat.
“Run along now, Sissy boy, before I call in one of the guys from the football team and have you suck him off,” she said as she slapped my diapered bottom.
“Yes Ma’am,” I replied obediently and hurriedly pulled up my silky shorts. I dried my tears and rushed out of the bathroom as quickly as possible.

After school, my mom came by to pick me up as she always did. I was dreading getting my diapers changed since it would be obvious I had been spanked and then I’d have to come up with an explanation that would keep her from giving me more of the same.
I stepped into the car with my pink silky shorts which immediately got my mom’s attention.
“Where’d you get those?” she asked as she pulled away from the curb.
“The school nurse,” I mumbled as I put my wet diapers and jeans on the floor in front of me, “she changed me at lunch.”
“Well, that was nice of her,” she said as she ran her hands over the front of my bulky crotch, “looks like she did a good job.”
I said nothing but noticed a bag on the floor. Picking it up, I saw three pairs of new pink plastic panties, with three rows of ruffles across their back.
“Oh. Those were on clearance so I picked them up for you. It’s getting harder and harder to find plastic panties in your size so I was lucky to get those at such a good price,” she said cheerfully.
My heart sank as I pictured the flouncy white ruffles gaily adorning the shiny pink plastic across my rump.
“But Mom!” I burst out in protest, “these are for girls!”
“Oh Jimmy, no one’s ever going to see them on you so what are you worried about?”
I didn’t tell her about the dozens of people who had seen my nursery print panties today and I felt my eyes filling with tears. I noticed we weren’t headed in the usual direction of home and I became a little panicky.
“Whe-where are we going?”
“Don’t worry Honey. We’re going over to Aunt Suzie’s house-“
“But she’ll see my diapers!” I cried.
“Jimmy. I had a long talk to her about your wetting and she knows all about your diapers. And there’s nothing to worry about, I brought over a change for you,” she explained as if that were my concern.
Aunt Suzie was my mom’s younger sister, a buxom woman in her late twenties whom I liked a lot. If it weren’t for the fat diapers I was wearing I would have been eager to go over to her house, but now…I was thoroughly soaked from such a trying day and I wasn’t looking forward to having her change me.
As if reading my mind, my mom reached over and slid her finger inside the leg of my shorts and plastic panties.
“My, you’re becoming quite a little wetter aren’t you?” she remarked.
I blushed but said nothing, biting my lip in embarrassment.
Before long, we pulled up in front of Aunt Suzie’s house. I waddled out of the car and followed my mom up the driveway, carrying the bag that had my diaper change and the new panties in it.
We rang the doorbell and my aunt showed up, beautiful as ever. I blushed again as she hugged me and reached down to squeeze the seat of my soggy diapers. In my heightened state of anxiety, I let loose with another stream of pee and squirmed uncomfortably.
“Well hello, baby cousin,” she said brightly.
My face was mashed into her tremendous breasts as my cheeks turned a shade of crimson.
“Jimmy’s change of diapers is in the bag,” my mom explained.
“Well, we better get our little baby taken care of then,” Aunt Suzie gushed as she pulled me into her house, “feels like mommy’s little boy wet himself.”
“Suzie, I’ve got to go but it looks like you’ve got everything under control. I’ll see you tonight,” my mom told her.
“Okay, see ya, Sis,” she replied.
When the door closed, aunt Suzie pulled me into her bedroom. She was wearing a snug blouse that hugged her full bust closely and a pair of tight jeans that showed how well she maintained herself. She sat me down on the floor and pulled my pink gym shorts down, tugging them over my shoes.
“These are cute shorts, Jimmy,” she said.
“They’re not mine,” I countered, “the school nurse gave them to me because my jeans wouldn’t fit over these diapers.”
My aunt giggled.
“Yes, I can see that,” she said, “well don’t you worry about that, I’ll get you changed and into a nice fresh diaper in no time.”
I blushed while she busied herself peeling down my nursery print plastic panties and unpinning my wet diaper. With a warm washcloth, she wiped my damp crotch and bottom, taking a good look at my still pink fanny.
“Looks like you were a naughty boy at school today, Jimmy.”
“Nuh-uh!” I stammered, “it wasn’t my fault!”
“Well, I suspect you had it coming” she said unsympathetically, “And sometimes little boys just need to have their bottoms spanked. But I’m afraid I’m still going to have to tell your mom about it.”
I shook my head in frustration as she slid three fresh diapers under my rump. After coating my tender fanny with diaper rash cream and sprinkling baby powder over my front, she pulled the ends of the diaper snug and pinned them up.
“There you are, Baby. A nice, soft diaper to keep you safe and protected,” she cooed as she pulled my new plastic rhumba panties out of the bag, “and here are your baby panties!”
I blushed hot red as she gathered the legs of the shameful panties and inched them up my legs, pulling them gently over my bulging diapers.
“Oh, aren’t those just darling,” she exclaimed admiringly as she stroked the shiny front of the pink panties, “but this ugly shirt won’t do.”
With that, she got up and went to her dresser, opening her drawers until she found what she was looking for.
“This’ll be much better,” she said as she held out a frothy nighty.
“No, I don’t want to wear that too!” I protested.
She ignored me as she pulled off my shirt and tossed I aside.
“But I don’t wanna wear that!” I repeated.
“I’ll give you a surprise, Jimmy,” she said trying to tempt me.
Taking my hesitation for agreement, she pulled my arms through and brought the nighty over my head. It was a frilly pink, semi-transparent frock that was short enough to leave my diapers fully exposed.
“Oh yes, that’s much better,” she said agreeably.
I didn’t think so and I sat sulking until she pulled me up by my wrist, sitting me down on the bed. She had a number of pillows arranged against the headboard and she sat down against them, making herself comfortable. Giving me a coy look, she began unbuttoning her blouse, revealing a deep cleavage and my first view of a woman’s bra. Her tremendous bosom looked as if it were bursting out of her cups and the tops of each breast was deliciously curved.
I gulped with nervous excitement as she slowly undid the clasp on the front of her bra, releasing her heavy boobs before me.
“Come here, little Sissy boy,” she said invitingly, giving me a seductive wink.
I crawled forward and she situated me so that I was looking up into her pretty face, her big boobs a mere inch before my face. With graceful moves, she pulled back the lace cup of her bra from her right breast and brought my eager mouth up to her nipple. I instantly began suckling eagerly and I was rewarded with her strange, but pleasant milk. I swooned with pleasure as she reached down and began softly stroking the front of my diaper over my plastic panties. My little wiener quickly became hard and my vision was filled with her big soft breasts and her smiling face.
“There, there, little baby, you just nurse like a good little sissy,” she cooed softly to me.
I nursed for several minutes in ecstasy before she switched me over to her other boob. I took my fill as she continued to gently rub my diapered wee-wee and moments later, I had a shuddering orgasm.
As I slowly opened my eyes, my aunt Suzie pulled her breast from my mouth and snapped the clasp on her bra, kissing my forehead as she did.
“And now it’s naptime, little baby,” she said sweetly as she pulled back the covers and tucked me in. In a state of relaxed bliss, I quickly drifted off to sweet sissy slumber.
My dreams were filled with tall, powerful women dressing me and treating me like a baby. I woke up a couple hours later only to find a squishy wet bulk between my legs. I felt my plastic-pantied crotch and was rewarded with the familiar feel of a soaked diaper. As I realized how soggy it was, I heard my aunt Suzie in the other room talking with my mom.
“He really is just a big baby,” she was explaining to her, “I think some little boys just never grow up.”
“You’re right of course,” my mom replied, “it seems like I’m having to start his potty training all over again. And I’ve been putting him back into diapers during the daytime now.”
“Perhaps stronger measures are warranted.”
“What do you mean?”
“I think you should start dressing him like the baby he’s been acting like. And treating him like one as well.”
“What did you have in mind?”
“He’s such a sissy, I would suggest dressing him like a little baby girl, complete with a short frilly dress and Mary Janes.”
“Jimmy?” my mom laughed, “he would hate that!”
“Maybe that’s what your little boy needs, to get him to start acting more his age.”
“But…where would I find clothes for him?”
“Leave that to me, I have a nice collection from my niece that will fit him nicely. They may be a little short but I think that’ll be just fine.”
“Sounds like you’ve got it all planned out,” my mom said agreeably.
“Let’s just say I know a sissy when I see one and he’s the biggest sissy I’ve ever seen. Would you like to see what I can do?”
“Oh, very much. Shall we wake him up?”
“Why not? Let me get a few things out of the other room,” Aunt Suzie replied.
After listening to this conversation, I grew very anxious as I realized they were going to turn me into a little sissy baby girl. But what could I do? Either one was strong enough to put me over their lap and spank me. I could easily visualize my pretty aunt taking me across her knees, pulling up my short frilly dress, and pulling my diapers down for a hard, stinging spanking. I shuddered at the thought!
The two entered my room and I saw my aunt was carrying a large pile of items.
“Well, I see our little baby is up,” she said cheerily.
“Pulling back the covers, she immediately felt the front of my diapers.
“Soaked again. You really are just a big baby aren’t you?” she asked.
I said nothing but looked down in shame.
“Well, we’re just going to dress you up in the same way you’ve been acting, Sissykins,” she told me, “but first we’re going to need to change those wet diapers. You’re lucky your mommy brought over another change for you.”
Her tone of voice had taken on a condescending edge and I felt like she were talking to a four year old.
Sitting me on the floor, she peeled my clinging waterproof rhumba panties down and off my feet. Next, she unpinned the sodden cloth of my diapers and pulled them aside, wiping my tiny penis and balls as well as my damp bottom with a warm washcloth.
“I think we’re going to have to start all over from the beginning,” she informed me as she slide three fresh diapers under my rump, “we’re going to start treating you like the little sissy baby you so obviously want to be.”
“But I don’t want to be that!” I whined.
Ignoring me, she shook a generous amount of powder over me and I took in the familiar scent as she pulled the sides of my diaper up and pinned them closed. Taking another pair of the rhumba panties from my mom, she shook them out and snaked them up my legs and then over my big, bulging diapers.
“There, that should hold you for awhile,” she said satisfied.
“Now, let’s just see what we have here for a little girl who still wets her diapers.”
From the pile of clothes she brought in, she selected a frilly petticoat, a white frothy mass of soft layers that formed a wedge where the hem flared out. She put it over my head and adjusted it until she was satisfied of the fit. Next, she took what looked like a little girl’s Sunday school dress and put it over my head.
“Nooo!” I squealed in protest as I put my hands up to ward off the humiliating garment.
“Young man!” she snarled, her voice becoming suddenly harsh, “in this house, you will do as you’re told. Otherwise I will put you over my knee and paddle that bottom of yours. Do you understand me?”
“Ye-yes, Aunt Suzie,” I said shakily.
“By the way,” she said as she continued putting the dress over my head, “it looks as if your little sissy here had gotten himself into some mischief at school. When I was changing his diapers earlier, I noticed his bottom was still red from a spanking.”
“Well, well, well,” my mom said as she crossed her arms and looked down at me, “looks like you’ll be going over my lap when we get home, young man,” she told me squarely.
“But it wasn’t my fault!” I pouted stubbornly.
“We’ll finish this discussion when you’re over my knee, Jimmy,” she assured me.
My Aunt smiled down at me as she pulled some white knee socks up my legs and fit some pink Mary Janes to my feet.
“I can’t believe how well these fit you,” she said brightly, ” I was afraid they’d be too small. Stand up so I can see how the dress fits.”
I stood up, the bulky diaper forcing my legs out a bit and the soft petticoat rustling silkily around me. My aunt pulled a bit around the hems adjusting the fit to suit her.
“Well, it doesn’t quite hide your diapers but I think that’ll be just fine,” she chuckled.
Taking a brush from her vanity, she brushed my longish hair into pigtails and clicked a big pink bow over each one.
“You actually make quite a cute little girl,” she told me as she looked over the full effect, “Here, look for yourself.”
Taking me over to a full length mirror, she stood me before it and my mouth dropped in disbelief. I looked completely like a little baby girl and no amount of tugging on my dress would hide my embarrassing diapers. Tears formed in my eyes and as I twirled around, I could clearly see the shiny pink plastic and ruffles covering my thickly diapered bottom.
“Mommy! I don’t wanna wear this!” I cried in shame.
“You’d better start getting used to it Jimmy, because this is how you’ll dress from now on. You couldn’t handle your responsibilities as a young man so now you’ll be treated like the little sissy baby you’ve been acting like,” my mom told me.
I stamped my feet in frustration as the tears spilled down my face. Just then, Aunt Suzie sprayed my with a bottle of perfume, a sweet, childish scent, suitable for a little girl.
“There, now you smell like a baby too, Sissy-boy.”
After my mom gathered my wet diapers and old clothes, we said goodbye to Aunt Suzie and headed home. I sniffled and sulked on the way there, wondering how my new life was going to be. It was late when we finally pulled up into the driveway and I was glad it was dark out. Nonetheless, as soon as I got out of the car, a breeze came and blew my dress and petticoats up around me, exposing my diapers even more clearly.
“Oh!” I cried, as I fought to bring the frothy layers under control. The breeze was chilly on my bare legs and I felt a small trickle of pee escape into my diaper.
“Come along, Jimmy,” my mom said as she took me by the wrist and pulled me inside.
“I want you to get ready for bed, you’ve got a long day ahead of you tomorrow,” she said as she slapped my diapered bottom, “If you’re going to be dressed like a little sissy girl, we’d better go shopping.”
“But I don’t wanna dress like this!” I protested.
“And I think we’ll start out tomorrow with a nice, hard spanking. That should do wonders for your attitude, Jimmy.”


Once a Sissy, Always a Sissy

As I sat on the bus making it’s way across town, I fidgeted nervously, pondering the events that had led me to this point. Last week, my first and only serious girlfriend had kicked me out of her apartment after she had caught me masturbating again.
Things had not gone too well for me with Jenny, starting with her discovery of my penis, or rather, the lack of one, in her eyes. I suppose I had been in denial about my diminutive weiner, which had never really grown much since I was in the second grade. It still was little more than a stub, even when it was erect, and it’s diameter was about that of my pinky finger. Of course, it didn’t help things that I was a premature ejaculator as well. These things all conspired to bring a my relationship with Jenny into a downward spiral and she immediately stopped giving me any sexual attention of any kind. At the same time, she started treating me more and more like a little boy but I guess I was so used to being dominated by strong women all my life that I just went along with it.
Two weeks ago, she informed me of her intention to start dating other men. When I protested, she responded by pulling me over her lap and spanking me with her hairbrush until I was sobbing like a baby. I should have left right then and there but I couldn’t. I guess I’ve always been weak willed and I kept rationalizing why I should stay with her so I just learned to accept the situation.
However, since I wasn’t getting any sexual gratification from her, I became increasingly horny and masturbation was the only relief I could get. One day while I thought she’d be away for a while, I found one of her Victoria’s Secret catalogs lying around. No sooner were my underwear in a circle around my ankles and I was readying myself for some badly needed relief, when Jenny barged in with one of her new boyfriends. To make a short story even shorter, she lost no time in yanking me over her lap and spanking the daylights out of me with her hairbrush again–in front of her boyfriend no less! After that, she kicked me out permanently and I was forced to walk all the way back to my mom’s house.
The masturbation episode was the last straw for Jenny and immediately after had she kicked me out, she called my mom up and told her everything, telling her I was nothing more than an immature sissy who needed his mommy. Needless to say, my mom was anything but pleased when I got home. I knew that for sure when she met me at the door with the paddle in her hands. She dragged me inside and after tearing my pants down, proceeded to give me my second blistering spanking of the day.
After a good cry and a ‘time out’, with my nose pressed into the corner and my trousers gathered around my ankles, my mom returned to the living room with a suitcase in her hand.
“Jimmy,” she said with great deliberation, “I’ve tried to do my best to raise you to be a decent young man. Apparently, I’ve failed in my task so it’s time for someone else to have a crack at the job.
“I’m sending you to live with my friend Vanessa who lives on the other side of town,” she informed me stonily.
“V-Vanessa?” I asked shakily as I rubbed my stinging bottom that was still bared and red as an apple.
“That’s right Jimmy, Vanessa. I trust her completely and I know she can handle a grown up sissy like you.”

Now, as I sat on the bus, still shifting uncomfortably in my seat because of the duel spankings, I pondered my new living arrangement.
I hadn’t seen Vanessa for years, not since I was kid, although I still remembered her with a strange mixture of arousal and humiliation. She had treated me to my first and only sexual experience when she had allowed me to nurse from her wonderful, massive breasts. Everytime I thought about it, my tiny pecker stirred and my heartbeat quickened. Back then, Vanessa had been a total babe, with an unbelievable body. I had been ten and she was in her mid-twenties which would make her mid-thirties now.
What did she look like now, I wondered. Maybe she’d let herself go and gained a million pounds, I thought absently. Maybe she was wrinkled and ugly, or just plain dumpy looking…
I would know very soon, I realized as the bus took me steadily closer to her home. If she was good looking, I was determined to show her the new me. Now that I was twenty and all grown up, I was in a position to be able to talk with her as an equal. This time, she wouldn’t be changing my diapers, and this time, maybe we could even go out on dates! I knew I was getting ahead of myself but I couldn’t help fantasizing with my memories of her. I pictured myself taking her to an elegant restaurant, and then back to her house, where I’d ravish her and kiss her wonderful bosom. Ah, if only I could make that happen!
The bus finally lurched to a stop outside a wealthy gated community and I took my suitcase and got out, introducing myself at the guard shack. The sentry let me in and gave me directions for the short walk to Vanessa’s house. Evidently, she had done very well for herself since I had known her, as was quickly becoming apparent by the expensive homes I was walking by. Holding the paper in my hands with her address written on it, I came at last to her house. It was quite impressive, with a Mercedes parked out front in the driveway and a fancy hedge surrounding the large yard.
Walking up the stone pathway, I rang the doorbell, with butterflies in my stomach. In the silence of the neighborhood, I could hear the clicking of high heels as they approached the door on the other side. My heart immediately began beating harder when the door suddenly opened.
A young woman of about eighteen, dressed in a french maid’s outfit stood framed in the doorway and she took my breath away. She wore 5″ high heel black patent leather pumps, dark silky hose that showed off her fabulous, long legs, a very, very short black skirt that flared out over a white ruffled petticoat and a low cut white blouse, revealing a pair of beautiful breasts that were pushed up into a mouth watering cleavage. She had a dark choker around her neck and her long brown hair was pulled back from her gorgeous face. As I stared up at her green, piercing eyes, my mouth opened and I tried to stammer out some sort of greeting.
She was the kind of girl who was quite aware of her beauty and despite her veneer of politeness, she looked down on me with obvious superiority and confidence, making me wilt in return.
“I’m-uh, ah, I’m…my name is, ah,-” I babbled incoherently.
“Jimmy,” she said sweetly as she broke into a smile that just about knocked me over.
“Er, Jim…is my name,” I said, trying to correct her.
“Come in, we’ve been expecting you,” she said as she stood back to let me in.
I stepped up into the house and was led into a fancy living room, lavishly appointed with furniture and art that looked like it cost a lot of money. Out of the corner of my eye, I watched the maid walking in behind me, her long sexy legs competing for my attention as well as her exciting breasts.
“My name is Barbie,” she said softly, making me want to melt, “I’ll inform Vanessa you’re here.”
I was totally captivated by this young, sexy beauty and I nearly drooled as she turned around and stode into the other room, her high heels clicking on the hardwood floor.
This was going to be great! I thought to myself as I pondered the best method to flirt with this knockout. Somehow, I had to put my experiences with Jenny behind me and score with Barbie at the soonest possible opportunity.

My mind was still reeling from the possibilities when I heard two sets of high heels coming my way. Standing up, I saw the tall, familiar figure of Vanessa come around the corner and my jaw dropped for a second time. Far from having put on the pounds, my former babysitter was awesome in every way! She wore a semi-sheer white blouse that looked like it was about to burst open from her massive cups, held in check only by a lacy white demi bra that could plainly be seen underneath. She had unbuttoned the first three buttons of the blouse which gave me a view of the deep line of cleavage that disappeared down between her incredible breasts where they were pushing against each other.
Below that, she had on a beige skirt that came down to a few inches above her knees, which hugged her slim form very nicely. Her high heeled open toed sandals revealed her immaculately manicured toenails.
I had forgotten how tall she was and when she came over to hug me, she mashed her big bosom against my chin, smothering me in a wonderful, erotic embrace. I was ready to die and go to heaven!
“Jimmy!” she said cheerfully, “you’re all grown up now.”
“Uh-huh,” I said as I relaxed within her strong embrace.
“Last time I saw you, you were still in diapers,” she commented with a knowing smile.
I blushed deeply, hoping she wouldn’t elaborate any further in front of Barbie, who I hoped was still unaware of my long and drawn out childhood that had been filled with diapers up until the age of fourteen.
“Er, a lot of things have changed since then, Vanessa,” I said meakly.
“Well, we’ll see,” she said with a smile as she patted my bottom affectionately.
I wasn’t sure what to make of that comment but in my fog of arousal, I brushed it off without further thought.
“Come upstairs, I’ll show you your room,” she said to me.
Barbie wandered off elsewhere and we climbed the curving steps that led to her upper floor.
My eyes were glued to Vanessa’s saucy bottom and her smooth, slender legs atop her high heels as she slowly ascended the stairway.
“This sure is a nice place,” I said in wonderment, trying to ease my excited tension from being in such close contact with two total babes.
“Thank you, I’m an investment banker for a financial institution here in town,” she informed me.
She sure didn’t look like any banker I’d ever met, I thought to myself.
She led me into the first door on the right which was a softly lit room, appointed in a very feminine fashion, but which was very typical of Vanessa. It was more girly than I would have liked but who was I to complain about free room and board?
I sat on the four poster bed and recognized immediately the sound and feel of a vinyl mattress cover under my rump. Why would that be here? I wondered.
For my fifteenth birthday, my mom had given me several pairs of training panties, to replace my daily diapers although I was still having a problem at night. By the time I was sixteen, I finally stopped wetting the bed although my mom still insisted I wear diapers and plastic panties to bed for another year, just to be sure. Had she said something to Vanessa, I asked myself. Again, I decided not to say anything about it. Maybe it was from someone else who had stayed here.
“I’ll just let you unpack your things, Jimmy. I run a pretty informal place here and Barbie usually eats dinner with us. That’ll be about six o’clock,” she told me as she stood with her hands on her curvy hips.
“Okay, thanks Vanessa,” I said, trying studiously to avoid staring at her boobs.
“It’s good to see you again, Jimmy,” she said smiling, as she bent down and kissed me on the cheek, leaving the impression from her lipstick there while I blushed furiously.
“Me too,” I stammered, feeling foolish and inadequate all over again.
After Vanessa left, I struggled to get my runaway libido under conrol and settle down, even though I wanted badly to sit down and diddle myself with the images of Vanessa and Barbie swimming through my head.
I began opening drawers to put my stuff away. I froze when I opened the top drawer which revealed a stout, oval shaped wooden paddle, with a double line of holes going down it’s length. I looked at like it was a cobra and my stomach tightened into a knot, my mind imagining it slapping my bottom while I was made to bend over Vanessa’s lovely lap. I shuddered involuntarily and closed the drawer.
I filled the second and third drawers with my clothes but then got another shock when I opened the bottom drawer. It was the tallest of the group and it was filled with stacks of soft, cloth diapers. On the right side of the drawer were stacks of plastic panties, in various pastel colors of pink, yellow, peach and lilac. With my heart pounding in my chest, I picked up one of the panties to check it’s size. Maybe they were for a kid, I hoped. My hope dwindled when I saw they were right in my size. Frantically, I threw it back and closed the drawer quickly. I could only hope and pray those weren’t intended for me although I had a nagging suspicion they were.

Dinner went well and I forgot about the diapers as Barbie showed that she was as good a cook as I’d ever experienced. We sat around talking until about nine when Vanessa drew me a bath and invited me to make use of whatever I needed. I relaxed in her tub and it seemed all my troubles had gone away as I soaked in comfort. Finally, when I was finished, I dried off and went back into my room, my towel wrapped around me. Vanessa was waiting for me there, with her back to me, and when she stood back up to face me, my mouth dropped open in shock. There, laid on the bed, was a changing pad, three diapers in a stack, pins, baby powder, and pink plastic panties.
“I thought I’d help you get ready for bed,” she offered very matter-of-factly, as if it were nothing in the world.
“Huh?” I exclaimed, “but I don’t wear diapers anymore!”
“Now Jimmy, it’s been a long day and I think we both know this is better for both of us. This mattress was twenty five hundred dollars and I don’t want to take any chances,” she explained patiently.
My heart sank as I realized that Vanessa’s perception of me hadn’t changed at all in the last ten years. To her, I was still a bedwetting child who needed to be fastened up into his diapers every night.
“But-but, I really don’t need them,” I tried to tell her.
“I’m sure you don’t,” she said, although her tone of voice clearly said otherwise, “but I think for tonight, we’ll just be sure, okay Honey?”
I hated being talked to like I was four year old, especially now that I was an adult.
“But-I-I,” I tried to protest as she removed my towel.
“Hush, Baby,” she said soothingly as she lowered my nude form over the stack of diapers.
I blushed beet red as my bottom came into contact with the bunny soft cloth underneath me. All the more so since she could now see my tiny penis plainly sticking up like a tan crayon. Looking down at it, she giggled and put her hand to her mouth to try and hide her amusement. I blushed even redder and Vanessa bent forward, her huge breasts swinging before me, mesmerizing me like a form of hypnosis.
“It’ll be our little secret,” she assured me as she took a handful of diaper rash creme and began smoothing it across my bottom. I bit my lip in embarrassment as she looked into my eyes while she did this most intimate procedure. When she had coated it with a thick, sticky layer, she rubbed her creamy fingers down my slippery crack, sending erotic shivers coursing through me. Baby powder followed and she wasn’t stingy with it as she covered my crotch and between my thighs with the softly scented powder, making a cloud rise up around me. Humming to herself, she drew up the thick cloth between my legs and pulled the ends together at my side.
“This is just like old times, isn’t it, Honey?” she said as she smiled down at me while she pinned the diapers shut with pink duckie pins.
“Uh-hm,” I said, too embarrassed to return her look. I felt like I was ten years old all over again, having my diapers changed by my beautiful babysitter.
Shaking out the shiny pink plastic panties, she gathered the leg holes and then began snaking them up my legs. When she reached the base of my diaper, I lifted up my bottom obediantly as she tugged the panties up and over the fat diapers, circling around my hips several times with her manicured finger nails as she worked the panties over the big, bulging diaper.
“This should hold you ’til morning,” she said, obviously satisfied as she snapped the elastic waistband with a flourish.
I blushed again while she held me close to her and hugged me, bringing my face into close contact once more with the softness of her big breasts. I breathed in the intoxicating scent of her skin and perfume and my head swam with desire, despite the intense feelings of humiliation that were washing over me.
After a moment, she stood up and pulled the sheets back, beckoning me to get in bed.
“Nighty-nite, Jimmy,” she said, “sleep tight, Baby.”
I waddled over to the bed and got in, the all too familiar feeling of thick padding between my legs and embracing my hips. As I moved around, the noisy vinyl sheets reminded me of their presence and I felt so childish that Vanessa couldn’t trust me in her bed without diapers and waterproof sheets.
With another kiss on the cheek, she turned and left the room, shutting out the lights as she went.
I sat there, staring up at the ceiling, wondering if I’d ever be treated like an adult.

That night, I had troubled sleep.
My dreams were filled with humiliation and visions of when I was ten. I was wandering around Vanessa’s house in a pink party dress and diapers, desperately trying to find my babysitter. I looked in every room but I couldn’t find her anywhere. All of a sudden, Brittany showed up from out of nowhere and she had a mean look on her face. I was terrified of her after all she had subjected me to, and my only response was to flood my diapers in a wild panic. She laughed mockingly at me and then she dragged me out into the living room where everyone had gathered. They all laughed at my appearance and made humiliating comments to me which only made me pee my diapers worse and that’s when I started crying like a baby. Suddenly, Brittany was approaching me with the paddle in her hands, a determined look on her face.
“Now I’m really going to give you something to cry about,” she said as she grabbed me roughly by the wrist.
“Nooooooo!!!” I cried.

Suddenly I awoke with a start.
Warm sunshine was streaming in through the lace curtains and I realized it was morning already. With a shock, I also became instantly aware of the soggy wet mass within my plastic panties–the all too familiar feel of soaked diapers.
Oh no!
I glanced up at the door and saw it was slightly ajar. I could hear voices nearby in the hall and I recognized them as Vanessa and Barbie. What was I to do? I looked around the room thinking maybe I could stash the diapers somewhere but then what? My mind raced as I tried to concoct a plan but I just couldn’t think straight.
Then, suddenly without notice, Vanessa came into the room. She was wearing a short, white halter top that hugged her big, bountiful breasts showing every curve in the most delightful manner. They seemed to be spilling out of the top and her spaghetti straps looked strained to hold her bosom in. A smile was on her face as she came in and stood next to the bed, bending over to greet me.
“How’s my little baby?” she asked as she started pulling the covers back, “did you have a dry night?”
Despite the fact that I was being treated to the most fantastic view known to Man, my mouth went dry and I clutched at the blankets with an iron grip, panic overwhelming me.
“Come on, Jimmy,” she said as she pulled downwards against my efforts, “I just want to check your diapers, Honey.”
“Uh-uh,” I pleaded but she tricked me. Instead of pulling downwards, she switched her grip and simply lifted up from the side, exposing my bare legs and diapers competely. Dropping the blankets, I threw my hands down in a futile attempt to hide the wet diapers from her.
Vanessa looked at them and then shook her head at me.
“Looks to me like you haven’t quite outgrown the need for your diapers, have you, Jimmy?” she said as she crossed her arms over her ample chest. This time, she was no longer smiling.
“I-I don’t know what happened,” I said haltingly, “I think I-I had an accident.”
Vanessa turned away and without a word, started pulling diapering supplies out of the dresser. In silence, she began arranging the items on the changing pad she’d laid out and It was becoming obvious that she was going to put me back into another pair of diapers for the day. That was something I just couldn’t tolerate. I was twenty years old, for crying out loud! I didn’t need diapers, and I sure as hell wasn’t going to let Barbie see me wearing them.
Pulling me out of the bed by my wrist, Vanessa stood me up so she could pull my plastic panties down.
“No way!” I shouted defiantly and I pushed her away belligerently.
All of a sudden, the room swam before my eyes and I found myself on the floor, facing up at Vanessa while stars rang around me. My head was pounding where it had hit the floor.
“Try that again and you’ll really be sorry,” she said, as she towered over me with her hands on her hips and her legs spread slightly apart. I don’t know where she learned karate but I wasn’t going to give up without a fight. I launched myself at her, only to go crashing against the far wall where she had deftly flung me like a ragdoll.
“Okay…okay…I give up,” I mumbled as I rubbed my aching head.
Vanessa grabbed my wrist again and she pulled me over to the bed, sitting down calmly as she hitched up her skirt.
“Vanessa? Is everything okay?”
My head jerked up to see Barbie, staring at me in my pink plastic panties and wet diapers, standing next to Vanessa, and my face turned three shades of purple.
“Can I get you anything?” she asked out of concern.
“Yes. Can you open that top drawer and get me the paddle? I have a naughty little boy here who’s wet his diapers and needs a spanking.” Vanessa told her firmly.
Barbie giggled and walked into the room. She was wearing a similar french maid outfit again with another pair of black stilletto heels and short mini-skirt. Reaching into the drawer, she took the wooden paddle and handed it over to Vanessa.
“This situation should be very familiar,” she said as she peeled my clinging pink plastic panties down my legs. I whimpered in fear as I held her gaze for a moment, the look of a little boy who knows he’s about to get a blistering spanking from a strong woman. My knees went suddenly weak and I felt unsteady on my feet. I glanced down at her two massive boobs jiggling within her top, then at the wooden paddle in her hand, and finally, into her dark, determined eyes. Once again, Vanessa had defeated me with diapers and now she was going to reduce me to a bawling crybaby in front of this beautiful girl.
With an abruptness that I wasn’t expecting, she yanked me across her lap and I landed with a wet squish. Looking over my right shoulder at Barbie, I whimpered meekly as Vanessa unpinned my saturated diapers, pulling them back between my legs. Drops of pee were dewed upon my bottom cheeks and the room filled with the humiliating smell of urine. I could feel the blood going all the way to my ears as I was overcome with shame.
“Well, well, Jimmy. I guess once a sissy, always a sissy, hmm?” she said as she readied her spanking arm.
I stared down at her high heels and sexy calves but before I could utter a response, the paddle seared itself onto my damp bottom.
“OW-WOW-WOW-WAHH!!!!” my eyes shot open and I cried at the top of my voice.
I immediately started bawling like a baby, kicking my feet frantically within the confines of my damp plastic panties.
The paddle landed three times in quick, stinging succession. I screwed my eyes shut and gasped for air as I beat the floor with my fists. This woman could spank!
“WAHHHH!! WAAAAHHHHH!!” I cried, my voice sounding high pitched and girlish.
Tears streamed down my face and I sobbed uncontrollably. I didn’t make any attempt to get off Vanessa’s lap because she was far too strong for me anyway. I knew this spanking would end only when she was ready for it to end.
“AH-HA-WAHH!!” I blubbered.
My legs kicked and kicked while the hard wooden paddle rained down again and again on my dampened rump, always right on target. She delivered each stinging slap with the impact of a squash player, causing me to buck wildly across her silky thighs. I felt so pathetic, bent over this beautiful woman’s lap, my wet diapers now exposed to both of them, while she slapped my sissy bottom repeatedly with her paddle. I had wanted so badly to impress my pretty babysitter from ten years ago and now, I was right back where I started, getting a good hard spanking while I cried like a baby girl.
Each angry slap from the paddle landed crisply, delivering more stinging pain to my already punished cheeks. When the face of each had been spanked a shiny, ruby red, she turned her attention to the sides, whapping and slapping them mercilessly while I wriggled helpessly beneath her. My soft, tender bottom was paddled to a glowing, fiery blaze, which prickled like a panty full of red coals.
After what seemed was an eternity, she finally stopped and handed the paddle back to Barbie.
I was too weak to get up, and I sobbed and cried, my chest heaving as she helped me to my feet. I hid my face in my hands in shame while I shifted my weight from one foot to the other. The heat emenating off my bottom could’ve cooked an egg and I howled miserably. I could only imagine what Barbie was thinking of me as she discovered what a miniscule pee-wee I had, which was mostly hidden within my modest bush.
Vanessa took several baby wipes and cleaned her thighs of the pee that had touched her legs until she was satisfied it was clean again. Standing up, she re-arranged my fresh diapers, a stack of three that had a soaker pad sewn down the middle. Taking my hand, she gently shifted me over and sat me down on the diapers, which caused me to erupt into a fresh torrent of tears. From out of my field of view, she brought a big pink pacifier over and pushed it between my quivering lips. I sobbed loudly as I accepted it meekly, feeling like a baby all over again.
Vanessa shook her head as she went about her business, smearing my bright red bottom with more diaper rash ointment while I cried shamelessly. Several good shakes of the powder followed, after which she pulled up my diapers and secured them closed with pink bunny diaper pins. I looked away in humiliated misery as she snaked a pair of pink nursery print waterproof panties up my shaking legs, tugging them over the fat diaper without regard to my feelings of shame.
Barbie stood silently watching all this, her hands on her hips, no doubt amazed at what a big baby I was.
When Vanessa was done, she stood up and looked down at me, an immensely satisfied look on her beautiful face.
“Okay, Jimmy. It’s time we got a few things straight,” she started.
She looked so strong and powerful, with her dark penetrating eyes, the firm look on her face, her big breasts thrusting out proudly, and her tall, imposing stature. I knew I would never cross her again. She was right–nothing had changed between us–she was still the all-powerful figure that would hold sway over my life, changing my diapers when needed and spanking my bottom when that was what I needed.
“First off, your mommy sent you over to me because she was fed up with you. She said you were an immature little sissy and I’m in complete agreement with her.”
I hung my head in shame as she revealed her true feelings about me.
“It is apparent that you need a firm hand to give you the discipline you so obviously lack. I will be that firm hand,” she said, her voice like bands of steel.
“You will wear diapers from now on, since you can’t be trusted without them. If you need to be changed, either I or Barbie will do it for you. You are not to touch your diapers by yourself, under any circumstances, do you understand me?” she said pointedly.
I nodded my head sadly and was rewarded with a hard slap to my face.
“OWWW!!” I cried out.
“You will address me as ‘Ma’am’ from now on, do you understand??” she demanded.
“Y-y-yes M-Ma’am,” I whimpered fearfully as I rubbed my stinging cheek.
“You will also address Barbie as Ma’am. Is that understood?”
“Yes Ma’am,” I responded quickly.
Barbie was smiling wickedly at me but there wasn’t a thing I could do about it.
“Good. Then gather your wet diapers and put them in the washing machine. Barbie will show you how to do laundry around here. We have a clothesline in the backyard where you can hang your plastic panties up to dry.
“I will have a further list of chores for you but for now, you can start with the laundry,” she said as she turned to go.
“Oh, by the way,” she said as she turned back to face me, “my lingerie needs to be hand washed. And don’t get any ideas about wearing the panties–they won’t fit over your diapers and I don’t want you stretching them out trying.”
I blushed from the humiliation of her insinuation while Barbie smiled back at me.
After Vanessa left the room, Barbie crossed over and slapped my thickly padded bottom.
“C’mon Diaper boy. I’ll show you where to get started.”

During the next several weeks, I began getting accustomed to my new status under Vanessa’s rules. I found her to be a lot more strict than I remembered and she, along with Barbie, enforced her domain with an iron hand (and a hard wooden paddle). I was made to go to bed at 9 pm sharp, my tv time and usage were severly restricted, I was required to take afternoon naps, I had to ask for my diapers to be taken down so I could use the toilet, and my list of chores seemed to grow daily.
Barbie, while being the official maid of the house, was only too happy to have me assume her duties, with her watching and supervising my efforts. She barely talked to me except to tell me something wasn’t clean enough or that it wasn’t up to her standards.
I, on the other hand, couldn’t keep my eyes off her. I never missed an opportunity to watch her walk and it didn’t matter if she was coming or going, she looked fabulous either way. Her short, poofy mini-skirt tended to bounce and sway with her saucy bottom as she strode around and I noticed that when she walked, she put one high heeled foot in front of the other, sashaying like a model down a runway. Of course, she was certainly good looking enough to be a model although I don’t know if she was or not. She had shapely, sexy legs that never failed to stimulate whether she was wearing black hose or fishnets, as was sometimes the case. I don’t know why Vanessa required her to dress so sexily, I only knew I loved it.
Of course, I would have loved it more if she felt the same way about me, but that was hardly the case. She was all business with me and never spared me a glance, unless she thought I was staring at her too much. She had slapped me several times when she had caught me ogling her fantastic legs or her luscious breasts and she had threatened worse if I didn’t stop. Nonetheless, that didn’t prevent me from watching her secretly as she moved about the house and just seeing her move was enough to make me become aroused. She liked to recline on the sofa and put her feet up on the coffee table while she made me vaccum the house. I would steal glances at her sexily crossed legs, admiring her stilletto heels from whatever vantage point I was at.
Even when she changed my diapers, she was strictly business with me. I suspect she’d never have touched me if she hadn’t been specifically required by Vanessa to do so while she was at work. She did a rather rushed job of it, making me pull my wet diapers off and deposit them in the hamper while she hurried me through the rest of my changing. In her haste, she sometimes stuck me with the diaper pins and she never apologized for it. More often, she chided me for being such a big baby and she scolded me telling me that if I were a real man, I wouldn’t be wearing diapers anyway. Of course, it was one of the few times where I could stare at her breasts without being slapped since they hung right in front of my face as she was changing me. I figured she was about a 36D by the look of them and she never failed to dress in such a way that they were displayed in the most erotic way. With her sexy push-up bras, the upper halves of her breasts were lifted up into two glorious mounds of smooth, youthful flesh, tempting me daily with their perky splendor. Her tops were always low cut so that when she bent over to powder me and pull up my diapers, I was treated to a fabulous view down the front of her blouse, allowing me to see the center of her bra and sometimes the lace of her cups when I was lucky. My little weiner often rose to the occasion although the sight of it only brought laughter and disdain from Barbie. She’d often pinch it painfully and laugh, showing me her perfect set of teeth between her delectable, full lips as she told me such a tiny penis belonged wrapped in a thick baby’s diaper, rather than be free for adult use.
Being in such close proximity to two such sexy babes kept me in a perpetual state of arousal. It didn’t help matters that Vanessa bought the softest possible diapers to keep me in and they conspired to caress my wee-wee all day and night in a torturously erotic embrace. The trouble was that I was rarely left alone so my opportunities for relieving myself were few and far between. Vanessa had made it quite clear that there would be serious consequences if she caught me touching myself and I didn’t doubt her for a second. However, working in the same house with the young and sexy Barbie day after day kept me constantly horny and frustrated.
Once, while I was dusting in Vanessa’s bedroom, I came across a framed picture of her in a bikini. Even at first glance, it set my heart beating wildly and my pee wee twitched inside its baby soft prison. Picking it up, I gazed longingly at her incredible curves, the sensual shape of her hips and thighs, her smooth, supple skin, the way the strings of her bikini bottom tied at the side, but more than anything, her big, beautiful boobs that were straining at her top. Words cannot begin to describe the glorious shape of her full, round breasts, barely contained in the small stretched triangles of the thin fabric of her bikini top. I marvelled at the perfection of her bosom and as I did, my little weiner began to grow, quickly attaining its full length of (almost) two inches.
By reflex, my free hand went down to stroke it over the cushiony padding of my diaper. Along with super fluffy, triple thick cloth diapers, Vanessa also bought the softest plastic panties and my efforts brought about an immediate reaction. My breathing quickened as I stroked the bunny soft, thick cotton padding and let my eyes linger over the bikini bound image of my governess. Darting my eyes at the door, I saw no sign of Barbie and I sat down on the bed to provide myself with some badly needed relief. In no time at all, I was swimming in ecstasy, my eyes mesmerized by Vanessa’s angelic body.
I knew I was taking a tremendous risk, but I couldn’t help myself. My diapers felt so caressingly soft and Vanessa’s picture was so sexy. Looking at her pretty face, I could easily imagine what she’d do if she caught me in here but I was quickly rising to a blinding climax.
Being a premature ejaculator, I came quickly and I splashed my little load of jizz into my waiting diapers. I panted deliriously from the orgasm and gulped at the intensity of it, my head spinning wildly. No sooner did I set the picture back down on the table when Barbie came around the corner.
“What are you doing sitting around?” she demanded, “get to work! When you’ve finished in here, I’ve got another list for you to start.”
With my face a bright red, I bolted up and murmured a quick ‘yes ma’am’, as I grabbed the pink feather duster and finished the table, hoping she hadn’t seen me in my brief moment of pleasure. As she strode back out of the room, I breathed a sigh of relief at my victory, giggling as I felt the warm sticky mess in my diaper that would remind me for the rest of the day of my secret success.

It was also during these first couple of weeks that I noticed other changes.
I was in the kitchen, hand washing Vanessa’s lingerie with Barbie close by, supervising my efforts. With my hands deep in a sink full of sudsy water, all of a sudden I felt a stream of warm pee escape into my diaper without warning.
“Oh!” I cried out, crossing my legs quickly to try and stop the flow.
“What’s the matter?” Barbie said suspiciously, looking me up and down.
“Nothing,” I said meakly as I blushed a deep shade of red.
That was the first time I’d wet myself and not even felt anything beforehand. While it was true that I was wetting my diaper occasionally at night, usually during the daytime, I’d have enough notice that I could ask Barbie to take me to the toilet to allow me to do my business. She’d watch while I made my tinkle and then she’d swat me on my bottom as I scurried past her so she could pin me back into my diapers. But this was a disturbing trend, not having any indication or inkling of what was about to happen, before it happened.
Two days later, it occured again, while I was hanging my plastic panties up on the clothesline out back. Suddenly, without any prior indication, I felt the front of my diaper growing wet and warm and by the time I was able to shut off the flow, the front of my diaper was well soaked. I ran inside, my eyes brimming with tears, while I struggled with what was happening. Had I completely lost all control over my functions? Would I need diapers the rest of my life? I paced back and forth in anxious concern as I pondered this latest event.
The next question was what to do about it. I knew Barbie would be furious if she found out I’d wet my diapers during the day. Two days ago, she’d slapped my bottom with the paddle when she found my first accident and I could already hear the disparaging remarks she’d have ready as she changed me in the bedroom. I could try and hide it all day but then Vanessa would find out when she changed me before bedtime. Odds are, she’d probably spank me for being such a sissy and I didn’t want to chance that. The way I saw it, Barbie would probably just yell at me but then that’d be it. That sure beat a stinging spanking from Vanessa so I figured that was the way I’d go.
However, during the tension filled hour in which I debated the issue back and forth, I couldn’t help but leak a little more and my frazzled nerves made it impossible to hold it back. It was also made more difficult by the fact that my diapers were already wet–my first reaction was to just let it go and pee some more. Pacing back and forth in the kitchen, I wet a little, bit by bit, until the pee began to seep back into the seat of my diapers. Several times, I started to go and find Barbie, only to stop myself out of childish fear. As the minutes ticked by, the pressure on my bladder only increased. I tried to relieve the pressure by letting out just a little but my diapers were getting wetter and wetter as the afternoon progressed.
Finally, I decided I couldn’t wait any longer.
Walking upstairs, I found Barbie in her room, bending over at the waist to get something off the floor. In her tall, black patent leather pumps, her legs were spread slightly apart and my eyes immediately went to her sheer, black panties that framed and hugged her perfect derriere in the most delicious way. I swallowed hard as I gaped at the fantastic image before me, trying to summon up the bravery necessary to tell her of my accident.
“Uhm…Barbie?” I inquired timidly.
She spun around in surprise, a look of anger on her pretty face.
“What are you doing there, you little panty pervert–spying on me?” she said accusingly.
“Oh no! No Ma’am!” I was quick to say, “I just walked in.”
“Well? What do you want?” she snapped impatiently.
“Um, well, you see-”
“I haven’t got all day, Diaper boy, what do you want?” she interrupted me brusquely.
My face reddened at this rude assault by such a sexy babe.
“I wet my diapers!” I blurted out. Tears started to fill my eyes again and she looked at me with a mixture of pity and disgust.
“You’re nothing but a big sissy, aren’t you?” she said, shaking her head.
I nodded, hoping it would get some sympathy from her. Whether it did or not, I wasn’t sure because she walked past me and out into the hall.
“Well, come on, Sissy-boy, looks like it’s time to change your diapers again,” she told me.
I blushed hotly, ashamed at myself for my infantile behaviour but I followed her into my room where the changing pad was still set up on my bed from this morning. Sheepishly, I clambered onto it while Barbie retrieved a fresh stack of diapers from the dresser. Coming back over to me, she began yanking down my plastic panties, shaking her head as she did so.
“Please don’t tell Vanessa, okay?” I pleaded desperately, hoping against all hope she’d agree.
Without a word, she unpinned the sopping wet diaper and pulled it out from under me as she held my legs high up in the air by my ankles. I saw her bend down to pick something up and then she hoisted my ankles back up into the air abruptly. Suddenly, I saw the paddle come swooping down, landing on my upturned bottom with a loud SMACKK!! I cried out in shock but she smacked me again even harder. I tried to kick my feet but she held them like a vice and she brought the paddle down again and then again. Gripping the vinyl changing pad for support, I burst into tears and howled in pain, struggling in her grasp but this time, she only slid the stack of diapers under my damp and stinging bottom. I whimpered childishly, while she smiled down at me wickedly.
“Oh, I’ll tell her alright,” she said as she sprinkled powder over my shriveled pee-wee, “I’ll tell her what a big sissy baby you are and how she should dress you up like a little baby girl.”
“Please, please don’t tell her that,” I begged her as hot tears trickled down my cheeks, “I couldn’t help it.”
Barbie ignored me as she pinned up both sides snugly and retrieved a pair of pink, ruffle lined plastic panties from the drawer.
“See these?” she said as she held them up for me to see, “they’re perfect for a big, diaper wetting sissy like you.”
I sobbed tears of shame as she snaked them up my skinny legs and over my fat, bulky diaper.
“Here you are, a nice wittle pacifier to make you feel better,” she said as she stuffed my pink rubber pacifier between my lips. I cried softly as I sucked on it, knowing deep down inside that what she was saying about me might be true.

That night, I didn’t get a spanking from Vanessa as I was sure I would. Instead, she merely sent me to bed early and predictably, I woke up the next morning with my diapers soaked again. Without a word, Vanessa changed me and left for work, leaving me alone with Barbie again.
Barbie seemed to relish humiliating me and she never passed up an opportunity to do so. Last week, she had made a point of making sure I was hanging up my plastic panties out on the clothesline, right at the time when the school kids were getting out of school. They walked by, seeing me in my t-shirt, sneakers and bulging diapers, and they laughed non-stop, taunting me and calling me childish names. In my state of panic, it was all I could do to keep from flooding my diapers.
Barbie also liked to make me go outside to get the mail. This meant walking a good distance out in front, in plain view from the street, where people would see me and my shameful diapers. Often, she would purposely wait until she saw someone coming by and then she’d send me out, locking the door behind me. It made me want to cry from the humiliation of it!
Today when I got the mail, I was fortunate that no one was around but when I ran back to the house, I noticed one of the packages was from a place called Babyland. The package felt kind of squishy like clothing and I wondered nervously what it might contain. Opening the door, I was glad to be back in the house when Barbie snatched the mail from me and handed me the feather duster.
“Get to work,” she ordered me, “you can start with the study.”
Wordlessly, I took the duster and walked away but I was aware of the angry stare at my back from Barbie. Over the last week, I had noticed a tension building between us which stemmed from my resentment at being bossed around by this girl who was both younger and physically smaller than myself. She lorded over me like I were her personal slave and she demanded absolute obediance. I knew it infuriated her when I didn’t say ‘yes ma’am’ to everything she said and I did it on purpose as my only means of getting back at her.
When I reached the study, I allowed myself a smug look of satisfaction for my small victory, and I plotted more ways of defying her whenever the opportunity should present itself.
I was so absorbed in my plans that I failed to hear the front door open. I also failed to hear Barbie’s friends as they walked in. It wasn’t until I heard numerous giggles behind me, that I finally broke out of my reverie.
At the moment, I was bent over, my ruffle covered plastic panties sticking up in the air when I heard them behind me. I shot up like a jack-in-the-box to see three girls standing next to Barbie, staring at my diapers and laughing in open amusement. I blushed hot red in embarrassment and tugged my t-shirt down in a desperate attempt to hide my frilly diapers.
“Stop it!” I squeaked in a shrill tone of voice.
Barbie had joined in the laughter and in my state of panic, I felt a hot stream of pee surge into the front of my diaper.
“Stop it!” I repeated frantically, sounding more girlish than ever.
“Stop it!” one of the girls said mockingly, imitating my wimpy tone of voice.
The other girls laughed all over again and my face turned a deep shade of red.
Barbie stopped laughing and she suddenly became serious.
“Jimmy. I want you to pull up your shirt and show the girls what it is you’re wearing there,” she ordered me.
“No!” I said hotly. I was angry and humiliated and I wasn’t going to let her get away with anymore of this.
Suddenly, the room fell silent.
“What did you say?”‘ she said slowly and menacingly.
I swallowed hard and wondered if I had made the right desicion.
“No!” I repeated, trying as hard as possible to sound firm and manly but my voice faltered and cracked with uncertainty.
The girls all looked at each other realizing they were in the midst of a showdown where only one of us could win.
“You will address me as Ma’am, little boy,” she said icily, her beautiful steely eyes drilling into me, “now get over here this instant.”
Her words hit me like a bucket of icewater and now real fear set in. Already I was questioning the wisdom of standing up to her in front of her friends but now it was too late. Unable to move, I stared back at her as I bit my lip in angst, holding the hem of my t-shirt down trying to hide my diapers. Deep inside of me, I carried a fimly ingrained and well placed fear of strong, determined women. I was on the verge of buckling in this contest of wills.
With slow, deliberate moves, Barbie reached over and retrieved a stalk of very thin bamboo that was in a decorative vase. It was about the thickness of a pencil and roughly three feet long.
“Get over here–right now,” she ordered me. Her voice was low and it made me shiver with fright.
Another surge of pee escaped and I let out a cry of despair as I crossed my legs.
“Now!” she barked, emphasizing her command with an abrupt slash of the bamboo stick. It hit the wall next to her with a sharp snap, causing even the girls to jump.
By now, I realized I had pushed her too hard. I was in big trouble and there was no way out of it. Whimpering in fear, I inched forward, afraid to do anything that might make her angrier.
“Pull your t-shirt up,” she commanded me.
“Yes, Ma’am,” I said, now completely subservient. I lifted up my t-shirt, allowing her girlfriends to easily see my frilly pink plastic panties, covering the thick, bulging diaper underneath.
“Now, put your hands on the arms of that chair,” she said, pointing to an ornate wooden chair next to her.
With great trepidation, I moved over to the chair and bent over it, placing my hands on the arms as I was instructed. My heart was beating frantically now in my chest and my mouth was parched from fear. Now, my diapered bubble butt stuck out for everyone to see and make fun of. Barbie came up behind me and began slowly pulling my panties down, drawing out the agony of my punishment and increasing my level of anxiety. When they were mid-thigh, she unpinned my diapers and pulled them back, exposing my bare bottom before the girls.
“Well, well, well,” she said as she discovered the wet cloth below my crotch, “looks like our little sissy-boy has wet his diapers again.”
Her voice was heavily condescending and I blushed hotly, my neck and ears growing red with shame.
“This is what happens when you disobey me,” she said evenly.
As I faced downwards, I heard the swish of the bamboo through the air and then it landed on my tender upraised bottom with a crisp wwwhoop!!
“OOWWWWW!!” I cried loudly, jumping up from my position.
“Get back down!” she ordered me, “if your hands move once more, I’ll make sure Vanessa gives you a good paddling when she gets home.”
That put the fear of god in me and I quickly put my hands back down on the arms of the chair, leaving my bare bottom in the most inviting position for her once again.
I yelped in pain and kicked my feet up individually as I struggled with the fierce stinging on my fanny. I couldn’t believe the intensity of the pain caused by the narrow strip of bamboo.
Whoop!! Swisshh-swat!!
I quickly burst into tears and began sobbing as my bottom now sported four angry red stripes across it’s round, youthful surface.
Swish-whap! Swattt! Swwwatt!
I held onto the chair while hot tears streamed down my face and I bawled like a baby. Barbie was a good aim and she never missed her target, no matter how much I thrashed around. The cruel strip of bamboo landed unerringly on my cheeks, raising crimson stripes with each searing impact. She took her time, waiting for me to move back into the best position before she let me have it again, slashing at my poor striped bottom mercilessly. One of the girls had moved around to see the look on my face and I clutched the arms of the chair miserably, wailing like a little girl, as Barbie whipped away at my fanny. I knew I looked like a big sissy crybaby but I just couldn’t help myself. My bottom was on fire!
At last, she stopped and put the bamboo back into the vase.
I sobbed and moaned while she pulled up the back of my diaper and pinned it tightly on either side. I felt her pulling up my plastic panties as I looked up to make eye contact with the pretty blonde in front of me. With tears streaming down my face, I flooded my diapers with streams of hot, urgent pee. The tension of the ordeal must have done it because I couldn’t stop myself this time. I remained bent over in my humiliating position as my diapers grew wet and warm, the pee saturating the front very quickly and then collecting between my legs, where the other girls could see it. One of them pointed it out to the others and they giggled at my humiliating display of babyishness. I just kept crying, half from the stinging pain that was throbbing on my bottom and half from the shame of what was happening.
I didn’t dare get up from my servile position, now that Barbie had clearly shown everyone who was in charge here.
“Stand up and face me,” Barbie commanded me.
With my face red and wet with tears, I stood up but was unable to look her in the eyes. My brief, foolish stand of defiance had ended disastrously, and my shame knew no bounds.
“Maybe that will teach you a lesson,” she said smugly, as she put her hands on her hips.
“Yes, Ma’am,” I said abjectly as the last stream of pee filled my soaking wet diapers.
“Good. Maybe from now on, you’ll show me the proper respect that has so far, been lacking,” she scolded me.
“Yes, Ma’am,” I sniffled.
“Now go to your room and get into bed. It’s your naptime, Diaper boy,” she ordered me like a four year old.
“B-but…my diapers are wet now,” I complained timidly.
“Too bad Sissy, you’ll just have to get used to it,” she declared.
“Yes, Ma’am,” I sobbed as I shuffled out of the room, completely defeated again.
As I walked by, she swatted me on my ruffle pantied bottom, causing me to yelp like a little girl.
Her girlfriends erupted in laughter.

More and more often, I found myself discovering strange packages that were arriving from places like ABWorld, LLmedico, Babyland and BigBabies.com which made me very nervous. Some were small packages and I assumed they were clothing but others were large, heavy boxes, and I could only wonder at what they contained. Worse than that was having to sign for the packages when UPS dropped them off. Barbie insisted that I greet the UPS lady at the door, saying I was the “baby of the house” and could sign for any packages. She would giggle and hand me the clipboard, often adding a humiliating comment on her way out.
At about the same time, workmen started arriving, doing some kind of remodeling to a room at the end of the hallway. Neither Vanessa or Barbie would tell me what it was but they made a point of locking the door when the workmen went home for the evening.
At about the same time, what little control over my bladder seemed to gradually disappear and it was impossible to hide the problem from Vanessa. All too frequently, I would soak my diapers during the day and of course, I rarely woke up anymore without my diaper sopping wet. Vanessa was fond of saying ‘once a sissy, always a sissy’ but there was nothing I could do to reverse the trend. It just happened suddenly and without warning, and before I realized what was going on, my diaper would be wet and warm and I was helpless to stop it. It really made me feel like a feeble baby to be dependant on diapers again and it left me angry and frustrated. Worse than that was having to wear my wet diapers for long periods of time before one of them felt like changing me. I came to looking forward to getting to wear a fresh diaper and being dry for however brief that might last.
Part of me wondered if these were the secret hopes of all sissies–simply to be able to wear dry diapers.

One night, I overheard Vanessa talking to Barbie about a double date that they were clearly excited about. Apparently they were planning on meeting two hunky men and they were determined to dress as sexily as possible for them. I did everything I could not to think about it but inside, I was burning with jealousy. Here they were going to go out and have a fun time, and I was going to be stuck at home, sent to bed early after being pinned into my sissy diapers. It was all so unfair! Not to mention that I was frantically horny. Well, I was going to show them!
I conspired and made plans to take advantage of their absence. I fantasized all day about going into Vanessa’s room, laying her bras on the bed and slowly stroking myself to orgasm as I looked at her bikini picture. It was the perfect plan! They would be gone all night and I would be free to do whatever I pleased. I couldn’t wait! Yes, I was frustrated with their freedom and the lack of mine, but at least I would get a dizzying orgasm out of it.
That evening, I did everything I could to make them believe I had nothing up my sleeve, although it hardly seemed necessary. Clearly, they had their manly dates on their mind and they barely paid me any attention at all while they got ready for their night out.
If I was horny before, these two succeeded in making me even hornier. I was frantic with lust as I serrepticiously watched them fastening their dark stockings up to their garter belts, hitch up their silky panties, and fitting their push-up bras to get the maximum cleavage. I nearly came in my diapers as I watched them dressing and they picked out their sexiest dresses to wear. Snug, form fitting little things that revealed the most skin and showed their luscious curves to maximum effect. Both of them did their make up so that they looked even more ravishing than usual, if that were even possible. In a way, I couldn’t wait until they left, so that I could finally masturbate myself to my heart’s delight. I was so excited!
My plan was to wait until they left the house. I’d pretend to fall asleep and then, after they’d left, I’d jump out of bed to begin a night of forbidden, wanton pleasures! It was all falling into place.
Vanessa, just like clockwork, came in to change me just like usual before bed. Even my soaking wet diapers couldn’t spoil her mood and she hummed merrily as she pinned me into another triple thick set of bunny soft diapers for the night. There was only one small difference. While she was waiting for Barbie to get ready, she insisted on making me drink a large baby bottle of warm milk. I tried to tell her I wasn’t thirsty but she only ignored me, and she held the bottle to my lips, forcing me to drink it while she waited. I never liked milk, especially warm milk, but even this drink tasted a bit strange to me. No matter. I’d do what she wanted because in ten minutes, she’d be gone, along with Barbie and I’d be free to enjoy my masturbatory adventures.
Vanessa was wearing a very low cut dress with a scoop neck and my little pecker was at full attention. She was so pretty and strong, and as she held the baby bottle to my mouth, her big breasts pressed against my face. I gazed impatiently at the deep crevice between her boobs, watching them rise and fall with each breath she took. I wanted so badly to stroke the soft surface of my plastic panties but I held back, knowing I had just another few minutes to wait before they were gone.
After I’d drank half the bottle, I tried to turn away but Vanessa kept the bottle positioned in such a way that I couldn’t escape it. I was forced to nurse from it like a baby and it was obvious I was going to have to drink it all before she’d remove the bottle. I felt a strange sense of euphoria as I sucked on the rubber nipple. I felt like such a baby, wearing my thick diapers that would soon be wet, and nursing from a bottle forced upon me by my beautiful governess.
At last, I finally finished the milk. A line of drool remained attached as Vanessa slowly lifted the bottle from my lips. Glancing at her watch, she smiled down at me.
“Sweet dreams, little Sissy,” she said in her most sexy voice.
For some reason, my limbs felt heavy and I could hardly keep my eyes open. The room went hazy as I watched Vanessa saunter out of my room, her sumptous derriere fantastically encased in the thin fabric of her short mini dress.
I seemed to be spinning downwards, into a pool of warm darkness and I was only vaguely aware that my plans had been defeated–there would be no masturbating and no orgasm for me tonight.
My last thoughts as I fell asleep were that I had once again, I had been outsmarted by Vanessa.

Several days later, I was still horny and frustrated, with no outlet for my sexual desires. I was so horny, I was ready to cry! I was desperate to get into Vanessa’s bedroom so I could masturbate to her picture and finally, on Saturday, I got my chance. I knew my window of opportunity would be limited so I wasted no time in doing my deed. In less than a minute, I had stroked myself to an earth shattering climax, only to have Barbie walk in on me just after I’d finished. I was still breathing a little hard but vastly relieved she hadn’t caught me.
However, she looked at me strangely and then walked out again. Consumed with guilt, I went out after her, only to find her whispering in her bedroom to Vanessa. When I walked in, the latter told me to come over to her. Today, she was wearing a short skirt with a slit up the sides, her chrome high heeled sandals, and a strapless top that pushed her huge bosom up into two wonderful globes.
Once again, my heart rate shot up wildly and I hoped there was no sign on my face as to what I’d just done.
“I want to check your diapers,” Vanessa told me straight out.
I racked my mind for some reason to stall her but I couldn’t think of anything. In my panic, I tried to force myself to pee and cover up the evidence of my misdeeds but of all times, nothing would come!
“But why?” I asked innocently, “I’m not wet or anything.”
“Come here, Jimmy,” she commanded me, her voice taking hold of me with its iron grip.
“B-but, why?” I stammered, even as I edged closer to her.
Without explaining herself, she reached forward and yanked me closer to her, making me cry out in fear.
“Oh!” I exclaimed.
With her long, manicured nails, Vanessa tugged down on my lilac colored plastic panties, lowering them to the level of my calves. My knees suddenly went weak as I looked up to see Barbie staring hard at me, her ravishing green eyes drilling into me accusingly.
Vanessa unpinned one side of my diapers and folded it down, revealing the gooey, sticky cum from my masturbatory misadventures. She took one disgusted look at it before looking up at me, fixing me with her withering stare.
“Barbie, would you be so kind as to fetch the paddle from Jimmy’s room?”
I immediately began fidgeting in front of Vanessa, the threat of a spanking weighing heavily on me.
“I-I didn’t mean it,” I offered lamely, hoping somehow that would make it better.
“You are going to get a good, hard spanking, Jimmy,” she said as she looked me in the eye, “and then, there are going to be some changes around here for you.”
My heart skipped a beat as I imagined what those would be.
“You are a naughty little boy who needs to have his bottom paddled. And after that, I’m going to give you a nice, hot, soapy enema,” she said as she looked deep into my eyes.
I quivered with fear and my little sphincter puckered in anticipation of it’s upcoming punishment.
“Oh no! I promise I’ll be good!” I squealed.
At that moment, Barbie returned with the wooden paddle in her hand and a big smile on her face.
“I’m going to enjoy watching you cry like a baby,”she said smugly.
I whimpered in terror as Vanessa pulled me over her lap, the gooey cum in my diaper pressing against me as if to mock my recent orgasm.
“No-no-please no!” I whimpered, “please don’t spank me, please!”
Vanessa ignored me as she rubbed my bottom with the face of the paddle.
“Aww…are you going to give us a big sissy cry now, Jimmy?” she asked demeaningly.
As if to confirm what she was saying, crocodile tears spilled out of my eyes and I squirmed as she removed the other pin from my diapers, revealing my bottom for the spanking it so badly needed.
“Mommy,” I whimpered weakly.

The spanking that followed was long, painful, and humiliating, and it left me bawling like a three year old girl who’d had her doll taken away from her and ripped apart. Vanessa paddled my bottom into a flaming hot, cherry red and every square inch stung like bees were attacking me.
As I lay over her lap, sobbing and trying to regain my breath, Barbie brought over a big, red rubber enema bag that she’d filled to bursting with hot, soapy water. I could see the suds and bubbles where the cap sealed the container and beads of water glistened from its bulging sides. She hung it from a hook on the wall and uncoiled the long white tube that was connected to the bag. At the opposite end, was a large rubber dildo that had a hole in the end where the water would soon be flowing out of. I gulped in fear as she swirled the thick phallus in a jar of nursery scented vasoline, coating it with a thick layer of the lubricant.
“No…no…no,” I begged weakly, as I tried to wipe the tears from my eyes.
Vanessa ignored me as she stuck her fingers in the vasoline and then brought them up to my anus, coating it well and pushing inside the rest as she pulled my reddened cheeks apart.
“I want my mommy,” I whined as I squirmed over her lap.
Taking the fat dildo in her right hand, Vanessa brought it up to my hole while the other hand kept my cheeks spread. With resolute determination, she began pressing it firmly against my sphincter, refusing to let me squirm away from it.
“Relax, Jimmy,” she said softly, “it’ll go in a lot easier if you just relax.”
“Oh!” I squealed, “it’s too big! I can’t take it!”
Vanessa kept up the pressure, bearing the fat, slippery dildo against my hole while she worked with my stinging cheeks to open them up wider.
“No! Please…it’s…it’s too…big…oh!…I can’t–”
All of a sudden, that fat head of the dildo slipped past my rim and Vanessa smiled with satisfaction as she pushed the rest of it slowly inside me.
“Ohhhhh!” I moaned.
“That’s a good little boy,” she commended me, “that’s my little sissy.”
She twirled it around slowly and began pumping it in and out as I moaned helplessly. I knew I sounded like a little girl but I couldn’t stop myself.
“This is just what a sissy needs,” she assured me as she continued to pump me with the slippery dildo, “and it’s something you can look forward to from now on, every morning.”
“Ohh…” I moaned in distress.
I felt the pumping motion stop and Vanessa’s hand went to release the clip. With a suddenness I wasn’t prepared for, the hot soapy water surged into my rectum and I cried out in surprise.
“Oh! Oh! OHH!!”
“There, there, Sissy. We’re going to get you all squeaky clean today,” Vanessa told me.
The water flowed into me with great force and I soon found myself in the throes of strong cramps. I tried desperately to pinch my stinging cheeks together in the hopes of cutting off the flow but it was hopeless. The fat rubber dildo was buried deep into my rear and the soapy water continued unabated.
I was panting heavily when she finally snapped the clip closed, allowing the first flow to work it’s way deep into my bowels. While she waited, she teased me with the slippery dildo, twisting it around and pushing it further in.
“I hope you enjoyed yourself today, Jimmy. Because that was the last time you’ll ever come in this house,” she informed me.
I bit my lip anxiously as I wondered exactly what she meant by that although at the moment, I was pretty well occupied with the water churning around inside me.
“How many times have you masturbated since you got here, Jimmy?” she asked as she pushed the dildo in deeply, making me moan in reponse.
“Um-uh…just f-four times,” I admitted.
“And did you always use that picture of me in the swimsuit?”
How had she known about that? And I thought I had been so sly!
With a thick dildo buried in my bottom and more soapy water waiting to fill me up, I couldn’t hold back the truth.
“Y-yes, Ma’am,” I replied meakly.
Vanessa smiled as she released the clip and the water flowed once again into my pouting bottom.
“Ohhhh!” I moaned.
“Well, I’m going to put a stop to that from now on,” she told me.
Beads of sweat appeared on my brow but tears filled my eyes as I saw my one chance for relief being taken away. I wasn’t sure how she would do it but I was certain she’d find a way.
Meanwhile the pressure continued to build inside of me and I felt like I was ready to explode. Vanessa squeezed the clip shut again and I lay there, panting over her lap, the cramps painful as the soapy water filled me up. I squirmed helplessly for several moments until she released it again. I cried softly until the last of the water flowed into me, gurgling with finality. I heard the bubbles disappearing into my rectum announcing the end of the enema and, after waiting an infuriatingly long time, she slowly removed the fat, imposing dildo from my anus.
“Ohh!” I exclaimed as it slid out of me.
“Go into the bathroom now and release that. And I better not find one drop on the floor or you’ll be going right back over my lap again. Do you understand?”
“Yes, Ma’am,” I replied obediently.
I limped weakly to the bathroom and practically fell on the toilet as I released all the pent up liquid. My cheeks stung bitterly where they contacted the seat but the relief from releasing the enema made up for it. Several times during the next ten minutes, I stood up thinking I was finished, only to feel another wave of liquid waiting to get out.
At last, I had completely expelled the enema, and slowly I made my way back to my room.
Barbie saw me out in the hallway, and she called me down to her.
“In here, Jimmy. This is your new room,” she said with a smile.
Butterflies filled my stomach as I walked slowly and hesitantly toward the room that had remained locked up and hidden from me for the last couple of weeks. When I turned the corner, Vanessa was waiting inside, a cool smile upon her pretty face. The room was made up like a little girl’s nursery, with the walls decorated with cartoon characters and frilly pink curtains on the windows. A big wooden baby crib dominated the room, painted in pink and I could see the waterproof sheet on its mattress, all ready for me. To its right was a raised changing table with more nursery print vinyl stretching over its shiny surface. Underneath lay stacks of diapers and in a shelf beside it were a wide selection of plastic and rubber panties. A pink dresser with bunnies on it was to the right of that and in the open closet, I could see dresses and baby clothes of every type imaginable. Lastly, a mesh walled playpen was off to the left side, its floor containing numerous baby toys.
My mouth dropped open in shock as I took all this in.
“From now on, this is where you’ll live,” Vanessa said firmly, “you’ll start each day with a hot, soapy enema and then we’ll dress you for the day like the sissy that you’ve been acting like.”
As I stood in silence, listening to her lay down the law, I held my hands over my privates since by now, I was only wearing my sneakers and a t-shirt.
“It’s obvious that you can’t be trusted wth adult privelages so I’m taking those away. From now on, you’ll be treated like a helpless little baby girl, who has no control and wets her diapers like any infant.”
Vanessa took me by the wrist and sat me down on the changing table as she began gathering a stack of diapers for me. Tears were trickling down my face as I looked around my new surroundings and then back at her.
“I don’t wanna be a baby!” I sobbed as I bunched my hands into fists.
Vanessa took a big pink pacifier that hung from a loop and stuffed it in between my quivering lips, passing the loop over my head.
“There. That will be your constant companion from now on. If I ever catch you without it, I’ll paddle your little bottom–do you understand?”
I nodded tearfully as I nursed on the fat rubber nipple in my mouth.
She tucked my diapers underneath me and proceeded to coat my crimson bottom with diaper rash ointment as she continued to scold me.
“Jimmy. Just look at you. You’re an immature little sissy who simply refuses to grow up. You belong in diapers so that’s exactly where you’ll stay.”
A cloud of baby powder rose around me as she sprinkled the front of me with it.
“And I want everyone who comes over, to see you as you really are, a diaper wetting panty-waist, trapped in the body of a man.”
She pinned my diapers closed securely and I sobbed in shame. Reached over, she picked out a pair of pink, nursery print plastic panties and quickly snaked them up my legs, fitting them over my bulky diaper with a bit of a struggle. With my bottom sealed up again within my waterproof panties, the stinging on my cheeks was increased measurably and I squirmed on the changing table in discomfort.
Standing up, Vanessa went to the closet where she returned with a pair of glossy black mary janes, their buckles, a shiny silver chrome. Untying my sneakers, she removed them along with my socks and threw both sets in the trash.
“What are you doing with my shoes?” I cried incredulously as the pacifier fell out of my mouth.
“These, are your new shoes,” she said as she held up the childish mary janes to me. I pouted as she stuffed the pacifier back in my mouth and pulled a pair of pink and white lace anklets over my feet. After that, she put the shiny black shoes over my feet and buckled them in place. I felt so sissyish as I looked down at the babyish shoes, with the lacey edges of my socks encircling my ankles.
Returning to the closet, she picked out a puffy petticoat with multiple white layers, each, softly ruffled so that it formed a flared out hem at the bottom. Taking my t-shirt off, she threw it in the trash as well and I squealed in protest through my pacifier. Ignoring me, she lowered the frilly confection over my head and adjusted the thin shoulder straps, making sure the layers of the petticoat fell evenly. Standing up again, she browsed the well stocked closet until she pulled out a lacey pink party dress, with short, puffy sleeves and white lace highlights all over it. I shuddered as I noted the short ruffled hem. Pulling it over my head she turned me around to button it up in back. All the while, I was whimpering through my pacifier while Barbie smiled down on me, smugly satisified with how things were progressing.
“Stand up, Sissy,” Vanessa ordered me curtly.
Sniffling to myself, I stood up on my babyish shoes and looked for the first time at the huge mirror that was covering the opposite wall. Looking back at me was an insecure little girl, pacifier in her mouth, her diapers and pink plastic panties plainly visible under the multiple ruffles of her party dress. Except that the little girl was me! Turning slightly, I noticed that the thick diapers gave my bottom a fat, round profile that only enhanced my infant look. I blushed deeply as I gazed at the reflection and it occured to me that I made a very natural looking baby girl, especially with my soft, feminine legs.
“Since you obviously still need your mommy, I will fulfill that role,” Vanessa explained, “from now on, you will address me as ‘mommy’. Do you understand?”
“Yes Mommy,” I replied submissively.
“The bathroom is now off limits to you. Since you can’t seem to control your peeing anyway, you can just use your diapers like every other little baby.”
“Yes Mommy,” I repeated.
Barbie led me over to a vanity and she began methodically putting small curlers in my hair, adding a foul smelling permenant solution before sealing each curl in place. I was angry and frustrated about the process but there was nothing I could do about it. It was still painful to sit down, even on the padded seat, and I sure didn’t want another session with Vanessa’s paddle.
While Barbie was attending to my hair, Vanessa busied herself by painting my nails a glossy, bubble gum pink, which gave my hands a distinctively sissyish look. I could only chew on my pacifier and pout as these two beautiful women transformed me into a prissy, sassy, sissy baby girl.
A half hour later, they were done, and they had me go out of the room and wait for the solution in my hair to take effect. Two boring hours later, they took out the curlers and fluffed my hair out. Peals of laughter ensued as the women snickered at me and my new Shirley Temple hair-do.
Barbie practically dragged me back into my new nursery so I could see the whole effect in the full length wall mirror. I blushed a deep shade of red as I witnessed in total, the full effect of my sissy transformation. I held the ruffled hem of my satiny party dress daintily with my pink tipped fingers as I realized my nursery print plastic panties were in full view below. My glossy mary janes gave me a childish look but the pacifier still in my mouth, along with my thick diapers, verified what I really was–nothing but a big baby.
Tears filled my eyes as Barbie led me over to my new playpen, sitting me inside with strict instructions not to get out unless I wanted another spanking. As I stared over the padded rail, I gazed at my babyish reflection and softly cried to myself. I stopped only momentarily as I felt the front of my diapers growing wet and warm. I was wetting myself without control again and I burst into sobs befitting my appearance.

The next day, Vanessa strode into my nursery with Barbie, a ravishing smile on her face. In her hand was a small plastic bag with something I couldn’t identify within it.
“It’s finally arrived!” she exclaimed as she dug her long nailed fingers into the clear manufacturer’s bag, “and just in time for your birthday.”
She pulled out a strange looking item that I didn’t recognize, a series of loops made from a type of soft braided cord.
“Barbie, be a dear and take his diapers down will you?” she asked her maid.
Barbie strode forward and pulled me out of my playpen, leading me toward the changing table where she sat me down, smiling wickedly at me as she did so. I had no idea what was up so I lay back and let her pull my plastic panties down, revealing my semi-wet diapers underneath. When she unpinned the cloth, Vanessa bent over and began positioning the loops of cord around my scrotum and penis. I looked down naively, not knowing what it was she was doing, as her smooth hands fiddled and adjusted the loops, securing them and cinching up them snugly.
“I had to get the smallest one they made, but even that was too big,” she explained to Barbie who watched with great fascination, “the man even asked me if this was for a little boy but I told him, no, just an immature little man.”
Barbie giggled and asked, “so how did you find one small enough?”
The nice man said he’d custom make one for me,” Vanessa told her, “he said anyone with such a tiny penis probably didn’t have any use for it anyway.”
On closer examination, I saw that one loop encircled my sack, another went around the base of my wee-wee, while another encircled it just a bit higher. They were all interconnected by a section of the cord.
Vanessa continued to adjust the device while I stood in helpless apprehension. I felt her cinching the loops tighter until they were snug, but not uncomfortably so. I wanted to stop her and stand up for myself but how? She’d just yank me over her lap and spank the daylights out of me.
Finally, she stood up and looked down on me to observe the results of her work.
”There,” she said, clearly satisfied, ”now for the true test.”
I stared down at my tiny pecker, now securely bound within the three loops of this device and I was seized with panic. The cord wrapped around my balls made it stick out slightly, now that it was encircled like a tie around a bag of candy and the ones around my shaft looked snug and secure.
“Okay Jimmy, let’s see you take it off,” Vanessa challenged me.
With the desperation brought on by the realization that I might never be able to play with myself, ever again, I clawed frantically at the corded loops, trying to tear the contraption off me. The material didn’t stretch in the slightest and despite its smooth feel, it had the strength of steel. Pulling mightily, the loops dug painfully into my balls and weiner as I tried to rip the thing off me. I gasped in pain and was forced to let go because of the agony I was inflicting on myself. Stamping my feet in frustration, I stormed about my nursery in a tantrum more like a five year old, than the adult I thought I was.
Barbie clapped her hands together and laughed with glee at my predicament. Vanessa smiled down at me with smug satisfaction while I made repeated attempts to prize even a part of my organ out of the device. At last, I gave up and slumped onto the edge of my crib in defeat.
“It’s not fair!” I sobbed, ”it’s not fair!”
“Jimmy,” Vanessa said suddenly in a very provacative voice.
I looked up from my misery to see her gazing at me with a seductive look I’d only seen once before.
Stepping over to me, she bent over slightly, hands pressed against the tops of her thighs, her immense breasts displayed in front of me within the confines of her tight, low cut top.
“Remember a long time ago when you were a little boy and I invited you for a closer look at my breasts?”
Her voice was soft and sultry with a timbre that was electrifying and as she spoke, her smooth, creamy hands began to caress her big, round cups sensuously. My eyes dropped to stare at what she was doing and I was hypnotized as I watched her stroking her bosom, alternately squeezing and lifting her boobs in a manner that drove me wild with desire. Vanessa was a living goddess with a heavenly body and her sexy game left me panting with excitement.
My little pee-wee responded immediately but no sooner had it begun to harden, than the restrictive diameter of the loops began to cut into my skin, preventing it from growing any larger. My sensation of sexual arousal quickly turned to unrelenting pain and I jumped up, trying once again to tear the restrictive device off me.
“Owwww!” I cried as my weiner battled in futility against its bonds.
“Take it off,” I begged her, ”please!”
Vanessa grinned down at me broadly, like a scientist who’d finally solved a vexing problem.
“Welcome to the sweet bonds of chastity. That should put an end to your masturbating nonsense, once and for all,” Vanessa proclaimed firmly as she stood back up straight, her hands on her hips in the classic posture of female authority, “happy birthday, Jimmy!”
“Serves you right, you big sissy,” Barbie said, still giggling.
“And now, it’s diaper time, Jimmy!” Vanessa announced cheerfully.
My lower lip quivered as I sat there, helpless and frustrated. I was desperately horny with absolutely no means of getting relief, and now entirely subject to the whims of this beautiful, but implacable disciplinarian.
I sniffed in resignation as Vanessa went about her usual thorough job of putting me in my diapers, the thick sticky layer of diaper rash ointment, baby powder, and soon she was pinning me up for my nap in my triple thick cotton diapers. A glittery pair of pink plastic panties followed and she finished by powdering between my thighs and the vinyl material of my panties.
“Beddie-bye, Baby,” Vanessa cooed as she slipped a full bottle of warm formula between my lips and began removing my mary janes. I drank the foul, tepid liquid submissively, still trying to grasp the enormity of the catastrophe that had befallen me. As Vanessa tucked my feet under the pink blankets of my crib, I think she sensed my misery.
Bending over me, she shifted my plastic pantied bottom across the crinkly waterproof sheet covering my mattress which in only a week’s time, had taken on the smell of stale pee.
“Don’t you worry, Honey,” Vanessa said soothingly as she held the big bottle to my lips, ”I’ll take care of those little balls of yours before they get too blue.”
Barbie giggled as if she were sharing a secret joke with Vanessa.
I wondered just what that might be as I drifted off to a troubled sissy sleep.

A week later, I had the opportunity to find out what she had in mind.
It was a Saturday afternoon and I lay awake in to my crib, still trying to get used to my freshly wet diapers from my afternoon nap. By now they were cool and clammy and they hugged my damp skin within the confines of my snug plastic panties.
It was also my birthday, and Vanessa had promised me we’d celebrate it in style. I was eager and hopeful that maybe today, of all days, she’d release me from my chastity for a brief, if fleeting, moment of pleasure.
My heart quickened as I heard the high pitched clicking of her high heels coming down the hall toward my room. I could tell by now who it was by the sound they made since both women had a distinctive stride. In this case, it proved to be both, and my suspicions were confirmed by the whispering I heard as they approached my door.
Vanessa came into the nursery, followed by Barbie, and she came across the room, unlatching the side bars of my baby crib. She was wearing a light green halter top, whose thin material stretched across her tremendous breasts tightly, leaving the entire curvy surface wrinkle free. I noticed her nipples poking out slightly and I could make out clearly, the outlines of her demi cup push-up bra. I prayed silently that she’d let me suckle once more from those magnificent, mouth watering mammaries.
Her small top left her firm, flat tummy exposed and below that, she wore a small pair of bun hugging white shorts.
Barbie, of course, was dressed in her obligatory french maid uniform, which was no less exciting.
I had to make a conscious effort now to restrain my penis which wanted desperately to react to this display of unbridled sexuality. To do otherwise was to invite a quick and painful reaction from my chastity device, which knew no mercy for my needs. I found the best thing to do was to think of other, non-sexual thoughts to try and distract myself and submissively bow to the reality that there was absolutely no way for me to relieve myself.
Vanessa pulled down my baby blankets, exposing my bare legs and bulging diapers. My pink nighty had worked its way up around my waist, leaving the colorful nursery print on my plastic panties exposed.
Instead of moving me to my changing pad as she usually did, Vanessa began peeling down my clinging vinyl panties there on the mattress, tossing them into the large diaper pail I had next to the bed. Even though it was emptied daily, my diaper pail added considerably, its pungent aroma of wet diapers to those of vinyl, rubber, and baby powder that normally permeated the nursery.
As usual, my diapers were soaked from my nap and Vanessa surprised me by humming an agreeable tune as she unpinned them. As she began cleaning my bottom and crotch, she didn’t immediately get another stack of diapers for me. Instead, she began the detailed proceedure for removing my chastity device, and after several minutes of work, my weiner was at last free. I sighed with relief and my excitement increased exponentially as she cleaned it with baby wipes and then put it aside.
Vanessa pulled back the baby blankets, exposing my nursery print mattress cover and instructed me get on my knees, facing away from her as I braced myself against the opposite side of the crib rail. I could only speculate what she had in mind for me but I knew it wasn’t a spanking or an enema. I was also made hopeful by her obvious good mood and I was sure she had something pleasant in store for my birthday.
“Now, I want you to be a good little boy and keep your hands on the crib rail. Can you do that for mommy?” she asked sweetly.
“Yes, Mommy,” I replied, trying to reign in my excitement.
“It’s very important Jimmy. I’m afraid if I catch you taking them off, I’ll have to give you a spanking,” she warned me.
“I’ll be good, Mommy” I said hopefully.
Looking over my shoulder, my bare bottom sticking out behind me, I craned my head to see what she was doing.
She appeared to be dipping something into the jar of nursery jelly but I couldn’t see clearly.
A moment later, I felt her prying my bottom cheeks apart with her fingers while she began coaxing something smooth and plyable into my anus.
“Ohh!” I squealed in surprise as I wiggled my fanny around.
“Stay still, or mommy spanks,” Vanessa warned me again, but her voice didn’t carry its usual threatening edge.
I settled down and the object slide in without too much difficulty. It was much smaller than the dildo nozzle she used with my morning enemas and didn’t stretch my sphincter to the limits.
As she moved it slowly in and out to find the right position, I moaned deliriously, the waves of pleasure washing over me. In a matter of seconds, I was panting hard and Vanessa stopped for a minute to allow me to cool down. My little weiner was rigid and begging for relief as it pointed downwards like the udder of a cow. Breathing heavily, I wanted so badly to reach down and give myself the relief I desperately needed but I kept my hands where they were, clutching the pink upper rail of the crib until my knuckles turned white.
When my wee-wee finally went soft again, a drop of pre-cum had appeared at its head and it slowly began to drool down towards the vinyl crib sheet.
“Okay, get ready with the cup,” Vanessa told Barbie, who was standing by with a shallow glass in her hands. I had no idea what her purpose was in all this but I quickly forgot about it as Vanessa began her ministrations in back again. I moaned deeply and pushed my bottom against her, trying to take the soft dildo as far in as it would go. She teased me mercilessly, never allowing me the satisfaction of feeling it deep inside my rectum, where I craved the sense of fullness. My penis was rock hard again and my breathing came in short gasps when Vanessa abruptly stopped again.
Sticking straight down, my pee pee twitched and flexed, frantically seeking release. Vanessa was patient however, and she stopped and waited for the inevitable to happen. Without further stimulation to sustain it, eventually my weiner began to shrink back to its usual limp length of an inch.
“Try it now,” Vanessa said to Barbie.
With a devious smile on her pretty face, Barbie bent forward and grasped my penis, pulling downward like she was milking a cow.
“Oh!” I squealed as I felt her handling it as if it were a tube of toothpaste she was trying to extract the last bit out of.
Her efforts were rewarded by a small, gooey string of cum that dribbled out of the tip, to collect in the small cup she held underneath.
I cried out in dismay as she not only deprived me of my joy juices, but also the explosive orgasm that would have accompanied it.
When no more semen could be extracted, Barbie stopped milking me and Vanessa resumed her slow, deliberate pumping of my anus. Tears of frustration filled my eyes as my weiner responded without regard to my wishes, growing hard again according to the will of Vanessa. Before long, I found myself once more at the brink of a mind shattering orgasm, struggling to bring it about on my own by grinding my hips against Vanessa’s hand that controlled the plyable dildo. She succeeed brilliantly in foiling my efforts, by simply relaxing the pressure whenever I tried to push against her. When I finally gave up in defeat, she’d resume her maddeningly slow massage of my prostrate, prolonging my erection in an unbearable torture of unrequitted pleasure.
When she finally stopped, my breathing was coming in ragged gasps and my face and neck were flushed.
“Please Mommy, please!” I sobbed as the tears of frustration rolled down my cheeks.
Vanessa smiled sweetly and stroked my bottom gently with her silky soft hands.
“There, there, Baby,” she cooed, ”we’ll get all that icky cum out of you, don’t you worry.”
Barbie giggled and bent forward, waiting for my tiny pecker to shrink back down.
In a frantic attempt to frustrate her efforts, I flexed my pee pee wildly, trying to reach orgasm on my own but it was like trying to catch the moon with a butterfly net. Clutching the crib rail with a death grip, I sobbed as my willy slowly softened and became limp again.
“Come on, Sissy,” Barbie said coaxing me with a mocking tone, ”cum like a big boy.”
I remained in my position, bent over and helpless as Barbie slowly squeezed more of my seed from my tormented penis. She managed to extract another big spoonful until at last, it went dry.
“My, that was a good one, Jimmy,” she said like she were commending a three year old on a successful potty attempt.
“I think that’s about as much as you’re going to get,” Vanessa advised sagely.
Barbie held the small cup in her delicate hands and gazed at the milky colored semen filling the bottom.
“What a good boy you are, Jimmy,” she said with feigned sincerity.
“You see, what we’ve done here is to remove all that pent up sexual tension, while still denying him any sort of release,” Vanessa explained as she grasped me by the hips and sat me down on the edge of the crib mattress.
“Now, as an experiment, to see how effective we were, we’ll just see if our little baby has any more get-up-and-go left in him.”
Vanessa took a bottle of Johnson’s baby lotion and squeezed out a small quantity in the palm of her hand. As I sat there whimpering and rubbing the tears from my eyes, she reached down and began slowly rubbing the lotion into my groin. My pee wee was so small, her hand dwarfed its limp form and she softly stoked it, but to no effect.
“There, you see,” she said as she pulled her hand away, revealing a well lotioned but nonetheless limp penis, ”no effect whatsoever. This sissy has been effectively milked.”
Barbie burst out laughing, her disdain and lack of sympathy washing over me like icewater.
It was all too much for me to handle and I burst into tears, crying like a two year old.
“Awww, there, there, Baby,” she said as she dipped the pacifier hanging around my neck into the cup containing the spent semen. She coated the big rubber nipple generously and coaxed it between my lips. Like the submissive sissy that I was, I willingly opened my mouth and accepted the creamy covered pacifier.
“Awww, poor wittle baby,” she said as she held it in my mouth, forcing me to suck and swallow my own cum.
“Oh,” Vanessa said as an afterthought, “this, is the best way to complete his milking.”
Taking hold of my arm, she pulled me up to an almost standing position and turned me slightly, so that my bottom was exposed to her side. Before I knew what was happening, I felt the searing impact of the paddle on my rear as she swatted me fiercely.
The pacifier shot out of my mouth as I shot up straight.
“OWWW!!” I cried in bewildered surprise.
Barbie burst out laughing and she took the paddle from Vanessa.
“You mean like this?” she said, her hand swooping down to deliver another stinging swat on my poor tender fanny.
“OWWW!! Stop it!” I wailed.
Barely surpressing a giggle, Vanessa took back the paddle.
“No. Like this,” she said as she yanked me over my my left arm and smacking me equally, if not harder than Barbie had.
“OW-HOW-WOW!!!” I shouted, dancing from one foot to another as my free hand went down to rub my reddening cheeks.
Barbie was laughing hysterically and she retrieved the paddle back from Vanessa.
“Oh,” she said between fits of laughter, “I thought you meant like this.”
Pulling my hand away that was trying to protect my defenseless bottom, she brought the paddle down hard, right in the center of my cheeks, leaving a bright red oval impression there.
I howled in pain and stomped my feet as the tears spilled down my face. By now, Vanessa was laughing too hard to continue the game so she sat me back down on the crib mattress as she tried to regain her composure.
“Sorry, Jimmy,” she said still chuckling, “but you have such a cute, spankable ass, sometimes I can’t resist it.”
I looked away and wiped the tears out of my eyes, trying desperately to keep a stiff lip through it all.
“Aw, cheer up Jimmy,” Vanessa exclaimed still giggling, “now it’s time to get you dressed up for your birthday party!”
She spent the next several minutes getting me secured in my chastity device and when she was satisfied that I was locked in and trussed up, she prepared my diapers for the day. I sucked my cum coated pacifier and sniffled while she slid the stack of soft, thick diapers underneath my rump, humming again to herself.
Normally, it would have brought about a painful reaction to look down at her big, swaying breasts, as she busied herself applying my diaper rash ointment and baby powder, but not now. Now that I had been relieved of my sissy juices, I could stare at her perfectly shaped boobs and not get hard or feel the accompanying pain. I could also allow my eyes to wander over Barbie’s immaculate body, savoring her glossy black stilletto heels and her long, sensuous legs. Her thighs were firm and trim and her skirt was oh, so short, threatening to reveal her silky sheer black panties if she bent over. And that’s just what she did as went over to get my socks and shoes for today’s outfit.
Even through my anger at her, I looked with longing admiration as she bent over and I saw her cute little bottom, nicely framed by the see-thru black panties stretching over her youthful cheeks. When she came back, she caught me staring at her and she came alongside the crib, the cup still in her hand.
“Ready for some more?” she asked, as she popped the pacifier out of my mouth and coated it again with the remaining semen. I twisted my face into a grimace of disgust but I obediently opened my mouth to take it back in again, my tongue once more tasting the creamy, somewhat salty sperm and the rubber of the pacifier nipple.
“How does that taste?” she asked as she bent over, revealing her wonderful cleavage as she did.
I said nothing but looked away as Vanessa was pulling the thick cloth up and pinning the sides of my diapers securely. She retrieved a pair of white, nursery print, plastic snap-on panties and she guided my feet thru as she pulled them up my legs. Getting to my thighs, she paused for a moment.
“Up, Sissy,” she commanded me.
I lifted up my rump in compliance as she worked the panties up and around the thick cloth of my diapers.
Bending over, she once again put her hands on the front of her smooth thighs to talk to me closer.
“Don’t worry Jimmy. Since you’ve got guests coming over to see you, I won’t make you wear a baby dress.”
I mumbled a sound of surprise through my pacifier, somewhat relieved by this unexpected turn of events.
“Nope. Instead, today you can be mommy’s little sailor boy. Doesn’t that sound like fun?” she said as if she were addressing a four year old.
I frowned in disapproval and she brought over a sissyish, baby blue colored satin top, lined with white lace and ruffled at the hem. The chest had a lace lined bib and puffy short sleeves with more lace around the edges. She raised my hands and lowered the softly lined top over my head and arms. In frustration, I tugged at the short hem of the top, hoping against hope it would cover my embarrassing diapers but that was not going to happen.
“Aww…you’re concerned someone’s gonna see your big poofy pampers, aren’t you,” Vanessa said in the most condescending tone of voice as she saw me tugging at the top.
I nodded my head numbly, unable to look her in the eye.
“Well I’ve got just the thing,” she said cheerfully.
Going over to the dresser she dug around until she found what she was looking for. Coming back to the crib, she held a frothy pair of white lacey satin rhumba panties before me, the lace on the seat edged with baby blue.
“Aren’t these just scrumptious?” she exclaimed with a ravishing smile.
I pouted miserably as she snaked the silky confection up my legs and over the smooth plastic of my waterproof panties. This was followed by a wide brimmed straw hat with a baby blue ribbon around its crown. At the same time, Barbie was rolling knee high socks up my calves and my glossy black mary janes over that. I noted that the socks had a satiny blue ribbon tied into a bow at the top of each sock. I couldn’t remember ever feeling like more of a sissy.
“Stand up Jimmy, so you can see your new outfit,” Vanessa said enthusiastically.
Pulling me up, they stood aside from me so I could see myself clearly in the wall mirror. Gazing at my reflection, I blushed deeply as I imagined what people would say when they saw me in this childish ensemble.
As if to confirm my fears, the doorbell suddenly rang.
“Oh!” I cried out in panic as a small stream of pee accidentally leaked into my fresh diapers.
Barbie giggled at my appearance without making ready to answer the door as she normally would have.
“Jimmy?” Vanessa asked sweetly, “wouldn’t you like to answer the doorbell? It’s probably one of your party guests.”
I blushed again and bit my lip in angst, then shook my head violently.
“Now, Jimmy,” Vanessa said, her voice taking on an edge, “don’t be rude. These nice people have come from a long way and they’ve brought presents for you. You wouldn’t want to leave them waiting would you?”
I looked up at her helplessly, praying she wouldn’t make me go through with this.
The doorbell rang again, its tone somehow seeming more urgent now.
Without a word, Vanessa picked up the oval wooden paddle and looked me in the eye.
“Maybe we need to have a little lesson in manners, hm?” she said, her voice cutting through me like a knife.
“No Mommy!” I cried frantically as the pacifier fell out my mouth again.
I bolted out of the room quickly, or at least, as quickly as I could, considering I had to waddle with the thick diapers I was wearing. I tried to shut out the giggling coming from my nursery as I went downstairs and to the front door. My heart was pounding in my chest as my hand went to the door knob. I could see the vague shape of two, slim young women through the glazed side window next to the door but I was frozen in fear. One of them rang the doorbell again and I heard Vanessa’s voice behind me at the top of the landing.
“Open the door, Jimmy,” she ordered me in her commanding voice that made my bottom tingle with fear.
As another small stream of pee leaked into my diaper, I opened the door and stood aside.
The two women burst into uncontrolled laughter as they took in my sissy outfit and as I stood there blushing, I recognized Brittany from my childhood grade school. After a moment, I realized the other one was Tammy, although both had changed quite a bit. I remembered them as two small girls, at the time, no more than ten, like myself. Now, they were about twenty and I was shocked at how they appeared. Brittany looked like a model, and she wore a fashionable silky dress that showed off her long, sexy legs. Tammy was now a beautiful blonde and she wore a black leather bustier that pushed her considerable bosom up into two fabulous mounds of femininity. As she laughed at me, I almost thought they’d spill out of her top as they jiggled from her mirth.
“Jimmy!” Brittany finally said when she could stop laughing, “you haven’t changed a bit! Still dressing up like a sissy and wearing your big, thick diapers!”
That comment made them burst into peals of laughter again.
“Couldn’t your mommy ever potty train you?” Tammy asked incredulously.
I glared at them angrily but remained mute as my face and chest reddened.
Vanessa came alongside and invited them in, thanking them politely for coming. Evidently, they were old friends and for a moment, I was forgotten as they chatted busily amongst themselves. She took them into the spacious living room and sat them down while Barbie brought them drinks. I endured more of their humiliating comments as Brittany related the numerous times she’d tricked me and gotten me spanked. Vanessa thought it was all a riot and she laughed along with everyone while I sat in silence, chewing my pacifier in frustration. Before long, the doorbell rang again and I was prompted to answer it.
Going to the door, I opened it up for another shocker. It was Ms. Taylor, my school teacher from the fifth grade! She was ten years older now but still a total knockout, and a classy one at that. She wore a sleek beige skirt and a white sweater that hugged her big bosom in a very form fitting way. As she saw me, she cocked her head little to the side in the cutest way and beamed in recognition of me.
“Jimmy!” she said as she came in and hugged me close, her large breasts pushing against me, “don’t you look darling!”
She didn’t seem to be surprised that I was still in diapers, at the age of twenty, and I was a bit put off by the fact that she obviously hadn’t had too much faith that I’d ever grown up. I guess she knew me pretty well, after all. As she hugged me, her hand went down to squeeze the ruffled seat of my diapers, checking to see if I was wet like she were my mother.
“It’s good to see you,” she said kindly and she planted a wet kiss on my cheek, leaving her dark red lipstick print for everyone to see.
In her hands, she carried a box gift wrapped in baby wrapping, with frollicking bears and lambs on its pink paper.
“I’ve bought you something very special that I’m sure you’ll love,” she whispered in my ear.
I blushed at the thought of that, fearing it was probably a sissy dress of some sort.
Ms. Taylor came inside and I noticed she was still quite a bit taller than me, particularly in her high heeled sandals. She took a seat on the sofa and Vanessa introduced herself and the others.
As they were making their aquaintances, the doorbell rang again. Vanessa snapped her fingers at me and I hopped up to go answer it.
This time it was my old adversary, Melissa and her equally tough friend, Tara. Both looked fantastic and as I stood aside, Melissa swatted my padded bottom with her gift, which was long and rectangular shaped.
“Ha!” she smirked, “looks like it works.”
I rubbed my bottom as they came into the living room to join the others. On the coffee table, the guests had stacked my presents, all wrapped in nursery print gift wrap, making it look more like a baby shower instead of my birthday. I wanted to run away and hide but Vanessa instructed me to turn around to model my pretty rhumba panties for everyone. Just when I thought I was going to die of embarassment, the doorbell rang once more.
I went to answer it and I was surprised to see my aunt Suzie standing before me. She wore a tight wrap around that hugged her delicious bosom, and a pair of short, Daisy Duke cut off shorts.
“My, my, Jimmy, I guess some little boys just never grow up, do they?” she said as she shook her head at my general appearance.
“It’s not my fault,” I tried to explain but she wouldn’t have any of it and she dismissed my excuse with the wave of her hand.
“Jimmy, you might be able to convince someone else that, but I know what a sissy you really are,” she told me in no uncertain terms, “I’ve always known you were a sissy and I’m glad Vanessa decided to put you back into diapers. That’s right where you belong.”
I was taken aback by my aunt’s blunt appraisal and I stood aside as she walked in with a gift under her arm. When she had taken a seat in the living room, everyone’s attention turned to Barbie, who was bringing in a birthday cake with pink and white frosting. I noted there were only two candles on it and everyone began singing happy birthday to me. I blushed as Vanessa came up behind me to tie a pink baby bib around my neck that said ‘Bedwetter’s Anonymous’ on it. They all laughed at that and she told me to blow out the candles.
“Jimmy’s twenty…going on two,” she announced to everyone’s amusement.
After serving everyone a piece, Vanessa spoon fed me my cake, while Barbie brought out a big bottle of warm milk for me to nurse from.
When all the ladies had finished their cake, Vanessa prompted me to begin opening my presents. Reluctantly, I did as I was told, and the first present turned out to be a pink patent leather sissy purse, with the words ‘Little Missy’ written on both sides in silver glitter.
“That’ll be perfect for when you’re out on the town,” Tara said with a disparaging laugh.
I blushed and put it aside, hoping that little adventure would never come to pass.
Pushing another big box before me, I felt Vanessa’s big breasts pressing against my back as she told me to open the next present. With much encouragement and giggles from my guests, I opened the childishly giftwraped covered box and found a frothy white baby dress, generously adorned with pink accents and lace throughout. It had a fancy layered petticoat sewn into it and it looked like it was made for a three year old girl except that it was obviously in my size.
Tara, who was sitting to my right, impatiently shoved her gift in my hands, a lewd smile on her face.
“This is one you’ll always have with you,” she said.
It had a strange feel to it, being about the size of my hand but a little bigger. When I tore off the wrapping, I discovered what looked like a short, fat dildo displayed in a plastic package, except that the base of it had a large plastic ring, exactly like a baby pacifier. The label on the package said ‘Dr. Cock’s Baby Pacifier’ and it showed a young woman wearing a bonnet and sucking on the product with an innocent look on her cute face.
I blushed as I imagined myself using such a thing but Tara wasted no time in grabbing it out of my hands and tearing open the package. She brought the big fat dildo up to my lips, pressing it against my face forcibly but I kept my mouth petulantly shut. Seeing my resistance, she slapped my bare thigh painfully which caused me to yelp out in distress and she responded by jamming the dildo in my mouth.
Everyone burst into laughter at her cleverness and she took the pink plastic loop and dropped it around my neck.
“There,” she said smugly, “guess you know who’s boss around here now.”
I sucked on the cock pacifier in mute humiliation, my cheeks buzzing with shame as I avoided the stares of all the beautiful women present who were witness to my defeat.
“That is so perfect for you,” Melissa said who was sitting to my left, “I always knew you were a cocksucker and now everyone else does too.”
I whimpered in embarassment as Ms. Taylor set her gift down before me. She offered me a sympathetic smile and I hoped her present might bring some measure of joy to this otherwise dreadful affair.
It was lightweight to hold and when I’d removed the giftwrap, I found a white box with tissue inside. Pulling back the tissue, I found three pairs of fancy ruffled rhumba panties, in pink, white, and lilac. They featured soft ruffles around the leg holes and big sassy layers of lace across the seat. I looked down at them in disappointment and then up at Ms. Taylor.
“I thought you might like to wear those for special occasions,” she offered sweetly.
The next present was from Tammy, Brittany’s childhood friend and willing accomplice. It was the smallest of all the presents there and it actually felt like two small cyclinders. Opening it up, I found one was a stick of Bonny Bell bubble gum pink lipstick and the other, a small sprayer of perfume labeled ‘Nursery Nights’.
Tara wasted no time in pulling out my pacifier and apply several thick coats of the bright glossy lipstick to my lips, before pushing the pacifier back in.
“Oh. That’s definately you,” she said, nodding her head.
The perfume, she took the liberty of opening and spraying me throughly with. It smelled like baby powder and something else I couldn’t quite put my finger on but it reminded me of my nursery and diapers. Even though I was already dressed like a baby, wearing a wet diaper, somehow this scent really brought it home to me and my face went bright red all over again.
“Now you smell like the sissy that you’re dressed up as,” she smirked.
“I know!” Brittany suddenly exclaimed, “why don’t we have Jimmy model his new dress and purse for us?”
“I think that’s a wonderful idea,” Vanessa said and she reached over and began unbuttoning my sailor suit top.
I squirmed in protest but soon she was replacing my sissy sailor suit with the frothy white baby dress, lowering it over my head despite my reservations. She buttoned it up securely in back and I noted in frustration that they were purposely put out of my reach. Lowering my silky rhumba panties down my skinny legs, she sifted through the box that Ms. Taylor had given me and selected a pink pair. They were a soft pink color with three large white ruffles crossing the seat and around the legs. At the top, in the front of the panties was a tiny white bow but stitched across the front, in fancy script, it said ‘Sissy Jimmy’. I wanted to cry when I read that and Vanessa happily snaked them up my legs, telling me, “you know Jimmy, people in life will judge you by the panties you wear. And these should make it clear just how much of a sissy you are.”
Lastly, she handed me my purse after putting my lipstick in it.
“There. You’re all set. This would be a wonderfull outfit for you to wear out in the park. I’m sure all the little girls would be green with envy,” she told me.
Everyone laughed at that and Vanessa made me parade around in front them. When I went by Tammy, she insisted on applying some blush to my cheeks, even though I was already several colors of red as it was. Several times, I felt my diapers growing wet and warm, no doubt caused by the trauma I was enduring at these women’s hands. I felt like such a babyish sissy, with my swishy white and pink dress, my bulging diapers covered by the pink lacey rhumba panties, my purse and my mary janes. I felt even more infantile due to the fact that my rhumba panties were helping to keep the wet cloth of my diapers pressed snugly against my skin. My shame knew no bounds as the girls took turns patting me on my ruffled bottom and making humiliating comments.
“There’s still one present to open,” Melissa said to the crowd, making my heart jump in fear.
She handed me the present she had been holding on to since she walked in. It was rectangular, about a foot and a half long, by four inches, and about 3/8″ thick. I sucked on my pacifier nervously as I held this particular gift in my hand, knowing instinctively what it was.
“Come on, open it,” Melissa dared me, a dark smile crossing her face.
Reluctantly, I ever so slowly tore off the paper and I revealed a polished wooden paddle, with two rows of half inch holes running down the length of it.
“Well! Jimmy already has one of those that gets a lot of use around this house but now we’ll have a choice of styles!” Vanessa stated happily.
“I say we give the baby his birthday spanking,” Melissa suggested impulsively to the group of women.
“Yes!” Tammy agreed,
“Excellent!” Brittany seconded.
“It’ll be fun,” Ms. Taylor suggested.
The girls all chorused their agreement until aunt Suzie raised her hand.
“But wait. I suggest we have Jimmy thank everyone individually and then they can give him his birthday spanks,” she offered to everyone’s enthusiastic approval, “let’s see, he’s twenty now and there are one, two, three, four, five, six…seven of us here. That means three spanks apiece.”
Brittany clapped her hands together in glee at the opportunity to spank me again and in a panic, I felt another stream of warm, wet pee go into my diaper.
Vanessa came over and stood me up, taking the paddle and handing it to aunt Suzie.
“Now, Jimmy. Thank your aunt Suzie for the pretty white baby dress,” she said as she pushed my reluctant form in the direction of my aunt.
I stumbled forward and pulled the fat pacifier out of my mouth as I stood before my sexy aunt, my pink sissy purse still in my hands. I tried not to be obvious as I gaped at her deep cleavage created by the tight wrap she was wearing but I think she saw me looking.
“Um, thanks, um, thank you for the, um, d-dress, aunt Suzie,” I stammered uncertainly.
“Well you’re most welcome, Sugarplum,” she said politely as she pulled my rhumba panties down to reveal my nursery print plastic panties.
“Jimmy? Have you wet your diapers?” she suddenly said accusingly.
I bit my lip nervously and looked away at the floor, slowly nodding my head.
“Looks like your birthday boy’s going to need to have his diapers changed,” she said to Vanessa as she took me over her lap, “thank god for side snap plastic panties.”
Everyone laughed at that remark except me who was quivering nervously as I clutched my purse, awaiting the first three slaps of the paddle.
I didn’t have long to wait. After pushing up the fluffy hem of my dress, she unsnapped the back of my plastic panties, pushed them back and unpinned my wet diapers. This kept the vinyl of my panties between her thighs and the wet cloth of my diapers.
Three times, the paddle swooped down, landing squarely on my damp and tender bottom. I gritted my teeth and fought to retain my composure, even as the tears began to fill my eyes. The last thing I wanted to do was to cry like a baby in front of all these women.
Lifting me back up, she instructed me to hold the front of my diapers and plastic panties in place so that I wouldn’t get pee on the next person’s lap.
I waddled nervously over to Tammy, who had taken the paddle from aunt Suzie.
“Thank you for the lipstick,” I mumbled barely audibly as I stood before her.
With a speed I didn’t think possible, Tammy swung the paddle and landed it on my bared fanny with a stinging ferocity.
“OOWWW!!!” I cried out, jumping up in shock and pain.
“What did you say? I couldn’t hear you,” she said with an evil smile.
“Tha-thank you for the lipstick and perfume,” I said obediently, in a much louder voice, my cheeks smarting badly now.
“You’re welcome, Sissy,” she said smugly.
I took my place over her lap fearfully, slowly getting myself situated with my diaper.
Despite my best intentions, I burst into tears and cried out like a baby, shaking my purse in a sissyish fury.
I jumped off her lap and carried my wet diapers and panties over to Brittany who quickly took the paddle and yanked me abruptly over her lap.
“Thank you–”
My required thanks were cut off by Brittany’s impatience to spank me.
I bawled openly now, my bottom on fire and I jumped up as the tears rolled down my face.
“Oops,” she said with mock sincerity, “I think I miscounted.”
Giggles filled the room.
Next was Ms. Taylor and she looked up at me with kindness and compassion.
“Thank you for the pretty panties, Ms. Taylor,” I said between sobs, hoping she’d be easier than the others.
Gently, she took me over her lap and waited until I had gotten myself and my diaper situated.
“It’s been quite awhile since I’ve seen your bottom from this perspective, Jimmy,” she said as she rubbed my red fanny appreciatively with the long wooden paddle.
I kicked wildly with my mary janes in pain and frustration as she slapped my already stinging cheeks harshly. Still gripping my purse, I jumped up and looked down at my former teacher who hadn’t given me any sympathy at all.
“Sorry Jimmy. But I didn’t want to show you any favoritism,” she said in her sweet, innocent voice.
I wiped the tears away and stumbled over to Vanessa who was waiting patiently for me.
“Well, little birthday boy. You probably didn’t realize it, but you’re already wearing my present to you. It’s your penis prison,” she told me.
The other girls laughed as she took me over her lap and I kicked even before she began spanking me.
“Settle down, Jimmy. Or mommy will really give you something to cry about.”
On and on it went, my poor botttom being smacked by everyone present until finally, I reached Melissa. I think I dreaded her most of all because she’d never shown me anything of her personality besides her bullying nature.
Now as I stood before her, my face wet with tears and my bottom a blazing red, I felt a last surge of fear-induced pee flow into my diapers. It was warm behind my hand and I blushed anew at such a humiliating sensation.
“Is there something you want to tell me?” she said, coaxing me provacatively in a syrupy tone of voice.
“Tha-thank you-for-for-giving me, the-the new p-paddle,” I said haltingly between sobs.
“It’s my pleasure,” she said wickedly taking me over her lap.
“Please don’t spank me hard!” I pleaded to her desperately.
I squirmed around on her lap desperately as the harsh wooden paddle landed on my punished bottom with a blistering sting. Thinking I was done, I tried to get up but Melissa held me down.
I cried like a baby, slinging my purse and pounding the floor as she kept spanking me, slapping my glowing globes with ever greater ferocity. I wanted to cry out that she was only supposed to spank me three times but I could barely catch my breath and when I did, I howled with pain, squalling like a little child.
I thought she was going to break the paddle on that last whack and my mary janes danced frantically on the floor as I kicked and cried. Bawling like a baby, I struggled to my feet, holding my wet diapers, plastic panties and purse before me like a sissy shield.
Vanessa held her arms out and I ran to her embrace, sobbing against her big, soft bosom as she held me close and stroked my head soothingly. I held her tightly, my new mommy, beautiful and powerful and so very strong. I looked up into her pretty dark eyes and I knew she would always know what was best for me. I sniffled loudly and cried, watching her chest slowly rising and falling as she reached down and took hold of my cock pacifier. Still whimpering softly, I watched as she brought it up to my lips and gently pushed it into my mouth.
“There, there,” she said soothingly, “hush, little baby.”
I had to open wide to fit the big dildo in my mouth and I blushed as I sucked on the big rubber cock head.
Slowly, she sat me down on the floor in front of everyone and re-arranged my wet diapers, pinning the squishy, saturated cloth back into place. I squealed in protest but she ignored me and re-snapped my plastic panties back into place, sealing in both the wetness and the fire on my bottom.
“Come here, Jimmy,” Ms. Taylor beckoned to me, “here’s your panties.”
Holding the panties up that went with my white baby dress, I went over and stepped into them. I must have lost them sometime while I was getting my spankings. Ms. Taylor pulled the stretchy pink panties up my legs and then over my plastic panties, adding to the effect that Vanessa had already started.

One by one, my guests said goodbye and Vanessa made me stand on the front porch and wave at them as they walked out to their cars. At one point, I noticed Melissa whispering to Vanessa and I cringed at what she might be discussing. It was early evening by the time everyone had left, with the exception of Melissa and Tara. At last, my former nemesis took me by the hand and led me upstairs where I was terrified as to what was going to happen.
“Melissa says she wants to see your nursery,” Vanessa had explained, but for some reason I didn’t believe her.
Opening the door, Melissa slapped me on my pantied bottom to get me in quicker. I stumbled in with my wet diapers clinging to my seat and crotch while Tara moved to close the door.
“It’s just like old times, ain’t it?” her trouble making, but attractive friend said threateningly.
I looked from her to Melissa hoping for some reprieve but none was coming.
I watched as Melissa tore off her mini-skirt with a haste that took my breath away, revealing a pair of high cut, black leather panties. For some reason, the dark, shiny look of them against her smooth, supple skin filled me with fearful anticipation.
Opening her purse, she produced a large, imposing strap-on dildo, at least ten inches in length and big enough that her fingertips couldn’t completely wrap around its massive circumference. It was extremely realistic in appearance with multiple veins running back from the big, shiny head. With a wicked look in her eyes that I’d seen before, Melissa stepped into the intimidating device and secured it around her sexy, curvy hips, making me gulp and suck feverishly on the fat rubber dildo pacifier in my mouth.
I watched her with a mixture of familiar fear and secret admiration. I had always felt a confused, yet deep seated envy for this strong, confident woman, despite her bossy and demeaning nature. With her long, powerful legs and big breasts, my will crumbled and I was easily intimidated. Just being in her presence brought about strong feelings of submissiveness and inferiority in me and I felt like a weak, little boy in his diapers.
She went over to my crib and swung the side downwards, opening it up for me. With her long, red tipped nails, she snaked my satiny rhumba panties down my legs and gathered them around my ankles. Leading me over to the crib, she bent me over and made me grasp the far bars, forcing my knees to the floor.
“Spread your legs, Sissy,” she ordered me tersely, “you’ve had this coming for a long time.”
I whimpered fearfully with my mouth full of rubber cock as she grasped the back of my plastic panties and yanked them down forcefully, unsnapping the double rows of snaps on either side of my panties with one quick pull and exposing my wet cloth diapers. Unpinning them impatiently, she pushed them down just far enough to give her an unobstructed access to my anus. I heard her coating the massive dildo with vasoline and my heart was beating wildly with nervous anxiety. My mouth went dry and my rear end puckered with anticipation as I waited for the inevitable, forceful invasion of my rump.
With my cheeks still hot and stinging, I felt her prying them apart and the blunt, sticky end of her dildo pressing urgently against my hole. I squealed like a little girl as Melissa applied steady, but firm pressure against my rosebud, trying to fit an impossibly big cock into my teeny passage. I tried to squirm away from her determined entry to try and prevent the gargantuan dildo from coming in and I was rewarded with several harsh slaps against my already smarting bottom. I cried loudly but the big dildo filling my mouth made my protests sound girlish and insignificant.
Finally, after several minutes of earnest, but unsuccessful attempts, I felt her halt her anal attack and she delivered an angry smack of frustration against my bottom cheek.
I howled in pain but was relieved in my belief that she had at last given up.
“Tar,” she said to her friend, “can you pull his cheeks apart so I can get this in?”
I quailed in fear at her implacable determination and I whimpered in terror around my pacifier.
Tara was only too happy to help and I felt her grasping both bright red cheeks in her hands, spreading them wide for Melissa’s big rubber cock. With another layer of vasoline quickly applied to its massive rubber head, she pushed it up against my defenseless back door, refusing to give up.
I tried to squirm away from the determined invader prodding impatiently against my anus but Tara easily held me in place, preventing any hope of escape.
Suddenly and inexorably, I felt the huge phallus slowly push past the ring of my sphincter and I moaned loudly.
“OOOOMMPHHH!!” I wailed helplessly.
I knew the skin around my hole had been stretched to the very limit, struggling mightily to accomodate such a monstrous dildo, and I gasped as it slowly slid into me. I felt like I were being impaled by a baseball bat and my toes curled as I put my head against the vinyl plastic of my crib mattress and lay in place, submissively taking my punishment. Rather than fight it, I lay obediently motionless, and let her push the monster deep into my rectum. With my face against the waterproof plastic, I breathed deeply the smells of vinyl and stale pee as Melissa slowly pumped my tender bottom. Gazing backward at the mirror covering the wall, I watched as she grasped my hips and forced herself deep inside me, making me moan like a little girl.
I looked like such a weak, effeminate sissy in my white fluffy baby dress and knee socks while she looked infinitely powerful, her strong, firm thighs flexing as she drove the fat dildo deep, in and out of my backside. Her big breasts hung down within her top, swinging back and forth with each punishing thrust of her pelvis. I grabbed my pink teddy bear and sucked frantically on the big rubber cock in my mouth trying to take comfort while Melissa proceeded to pound me from behind. I watched in the mirror as she thrust her strap-on in again and again, reaming my poor sissy hole with her tool. Tears of frustration trickled down my face as she buried her faux cock deep into my rear end, driving it in until it bottomed out and then she’d hold it there, forcing me to feel every inch and refusing to let go of my hips while I squirmed and moaned. At the same time, my little trussed up penis was receiving it’s own share of torment. With by backdoor being filled to capacity and pumped like never before, I wanted nothing better than to obtain sexual release, if only briefly.
My chastity device seemed to mock me without mercy and its bonds cut into my little package as Melissa rammed me again and again.
“OOOMPHH! OOMPHH!!!” I cried as Melissa smiled down on my sissified pose.
I sobbed with humiliation and groaned as my little pecker strained against its bonds, trying to get hard but completely unable to do so. It was so incredibly frustrating, being humped without mercy by stern, strong Melissa, and unable to get any kind of relief for myself. I gripped the crib bars and sucked harder on the the fat dildo pacifier filling my mouth, gasping to take in air.
Stepping up her pace, Melissa forcibly pounded my fanny remorselessly. I watched her clenching her teeth in intense determination as she hammered my bottom with deep, powerful thrusts. My body bucked while my bottom quivered and I had to grip the crib bars just to hold on while she drove the massive dildo in and out. I squealed and moaned at the top of my lungs, my poor rear getting the reaming of its life. A fine patina of sweat had appeared on Melissa’s forehead but she kept driving away in earnest, her boobs shaking mightily and threatening to spill out of her top.
It was then, that I caught movement out of the corner of my eye. I saw the nursery room door open and framed in the doorway was Vanessa. At last! My new mommy had come to save me, save me from this punishing ordeal! My hole was sore and it ached from being stretched so mercilessly. I was desperate for her to be my saviour and save me.
Melissa saw her too but she never missed a beat and she just kept pounding away at me, driving the dildo like a jack hammer into my back hole. I saw Vanessa smiling and nodding in satisfaction, apparently pleased by the fact that I was getting humped good and hard.
Finally, after I thought my hole couldn’t take any more, Melissa cried out in orgasm, and she plunged the dildo in as far as it would go, holding it there while she spent herself. I struggled to get out and away but she held me in place, forcing me to savor the big rubber cock buried deep inside me. At last, after she’d caught her breath again, she eased it out and I sighed with relief. My poor butthole was throbbing and my penis was in pain from the constrictive chastity loops. Vanessa walked in and rolled me over, checking my little weiner closely.
“Works like a charm!” she beamed at the others who broke out into giggles.
Melissa undid the strong harness straps of her strap-on with the practiced ease of someone who used it regularly.
“All done?” Vanessa asked her.
“Yeah,” she said, still breathing hard, as she looked down at me with a leering smile, “for now, I am.”
“Well, I’m sure Jimmy would love to thank you personally but unfortunately he’s got his mouth full of cock right now,” Vanessa told her jokingly.
Tara and Melissa burst out laughing and then Vanessa moved me over to the changing table to take care of my diapers. Melissa was cleaning her tool like a professional, wiping down the long, thick shaft with baby wipes until all the vasoline had been removed.
“Thanks for calling me,” she said to Vanessa, who was busy smearing diaper rash ointment across my red, spanked bottom.
“Don’t mention it,” she replied as she slid a stack of fat diapers under me, “anytime you want to come over and do it again, just holler. I’m sure it will do him a world of good.”
My heart sank as I contemplated further sessions with Melissa and her strap-on. It was going to be a week before I could walk normally again!
The three hugged and exchanged kisses while I sat on my arranged diapers, waiting for Vanessa to finish. When they left, Vanessa returned to getting me ready for bed.
“Well, you certainly did have a wonderful birthday, didn’t you?” she said with a big smile on her beautiful face.
With my lips wrapped around the rubber cock filling my mouth, I wasn’t in a position to contradict her and soon, my diapers were being pinned into place and a pair of plastic panties drawn up my legs. My satin rhumba panties had been put away for the night but she found a babyish pink nightey that was soft and comfy and she helped me into it. Putting me back into my crib, she pulled up the baby blankets around me and raised the crib bars, latching the side shut with a secure ‘click’.
“Nightey-nite, Sissykins,” she said softly as she walked out of the room, turning off the lights as she went. It was only seven o’clock and I was left in the quiet of the room, my only companion, the Barney nightlight on the far wall.
As I pondered the events of the day, I saw the nursery door open once more and an unfamiliar figure was backlit by the hallway. Pulling down my blankets, I sat up to see who it was that was walking in and staring at me.
“Jimmy? Is that really you?”
I froze in place, as I realized the voice belonged to my mother.
Whereas she was silhouetted by the light behind her, I was fully illuminated and she stared down at me in shock with my baby clothes and sissyish appearance. When she’d last seen me, I had had the look of an adult man but now, with my girlish Shirley Temple hairdo, frilly nightey and thick diapers, I looked like a three year old toddler girl. I gulped in fear and apprehension at her seeing me like this.
Pulling down my blankets the rest of the way, she exposed the shiny nursery print plastic panties I was wearing over the super thick diapers clearly visible through the filmy fabric of my nightey. Gripped by panic, I proceeded to flood my fresh diapers. My eyes began to tear up as I felt the spreading wet warmth that I was helpless to stop.
Putting her hands on her hips, she stared down at me angrily.
“Well. I guess I always knew that you were a sissy but I never realized the extent until now.
“Still wearing diapers, I see,” she said in disgust, “and wetting them like a baby, from the sounds of it.”
I hung my head in shame as the pee saturated my crotch and began to seep back between my legs.
“And what on earth is that in your mouth?” she suddenly asked incredulously.
I blushed three shades of red as she popped the cock pacifier out of my mouth roughly. I had been sucking on it for so long, I had simply forgot it was in my mouth.
“Mommy!” I cried out, suddenly bursting into tears as I continued to soak my diapers in a display befitting my infantile appearance.
“Don’t mommy me, you big sissy baby!” she snapped angrily, “it’s obvious you still need diapers and the kind of discipline that only Vanessa can provide for you.”
I pouted in silence as my mom scolded me like a child.
“I guess it’s true what they say,” she continued, “once a sissy, always a sissy.”


Jimmy’s Return to Diapers

When I was ten, I was still small for my age and frail, by most standards. My mom wouldn’t have dreamed of leaving me alone in the house, so whenever she needed to go somewhere, she’d drop me off at a friend of hers who lived in the neighborhood. This woman, who was twenty five or so, did most of the babysitting for the kids on our street. I remember her as being a total knockout, dark haired, and very curvy, if you know what I mean.
It was an average morning that I was introduced to her…

“Come in Jimmy, it’s nice to make your aquaintance,” she said to me cheerfully.
I was, by nature, very shy and I was unable to hold the gaze of this extremely pretty woman. I mumbled something but kept my eyes downcast.
“Don’t worry about him,” my mom assured her, “he’ll warm up to you once you’ve had a chance to get to know him.”
“Well he certainly is a little cutey,” she remarked as she ruffled my hair.
We went inside and my mom made small talk with her until it was time for her to go. I was a little nervous about being alone with a stranger, especially one so beautiful and sexy as this woman but it sure beat old Mrs. Snagworth, down the street. She was a crotchety old keister my mom once made me stay with and all I ever got out of that arrangement was a hard spanking.
This woman, who’s name I learned was Vanessa, was certainly different, with her snug shorts and tight crop top. I had never seen a woman who was made like her and I found it impossible to take my eyes off her big, bountiful breasts. I didn’t know at the time what cleavage was but instinctively, I realized I liked it.
Closing the door behind her, she bent down, offering me a breathtaking view, and taking my hand very sweetly.
“Jimmy, I want you to come into the other room with me so I can get you changed,” she told me.
“Cha-changed?” I asked dumbly, ” but…I’m already dressed.”
“Jimmy, in this house, we have a rule. All little boys have to wear diapers and plastic panties until they can prove that they don’t need them.”
My mouth hung open as she led me down the hall and into another room.
“B-but I don’t need d-diapers,” I insisted shakily. My heart starting beating much faster and I hoped she hadn’t heard the uncertainty in my voice.
“Well, we’ll see Jimmy. Last week I had a little boy over here who ended up wetting his pants and I dont want to take any more chances.”
She lifted me up onto the bed and began untying my shoelaces.
I felt my eyes begin to moisten and my cheeks redden with embarassment.
“But I don’t wet my pants!” I protested.
“That’s good,” she said as she pulled my shoes and pants off, “then you’ll only have to wear diapers for this afternoon. After that, you can go back to wearing your regular clothes.”
My lower lip quivered and I pouted helplessly as she slipped her beautifully manicured nails inside the waistband of my underwear and slid them down my legs. I gasped as my privates were exposed and my hands shot down to cover them. Vanessa smiled at me and took several cloth diapers from a stack and arranged them on the bed next to me. I gulped as I saw how thick they were and my heart beat even faster as I imagined having to wear them.
Taking my feet in her left hand, she raised my legs and slid the stack of diapers underneath my rump, laying me down on them gently. They felt bunny soft on my fanny and she held my hands aside as she shook baby powder over my groin and between my legs. From a flat jar, she produced two large diaper pins, with a duckie design and she put them between her full lips. Pulling the thick cloth up between my legs, she held the corners together snugly as she snicked the pins closed.
I bit my lip in embarrasment as she went over to a drawer to get something else. Thinking I was done, I sat up and got ready to get off the bed.
“Not yet Jimmy, you still need some plastic panties,” she said cheerfully.
I winced as she brought over a pair of white nursery print waterproof pants and held them up to me.
“These should be just your size,” she said with a big smile.
I wimpered in humiliation as she gathered the leg holes and began snaking them up my legs. I felt so babyish as she pulled them up my skinny thighs and then over the very thick diaper that was pinned on me.
“There!” she said as she ran her fingers around the elastic waistband, “a perfect fit. It’s as if they were made just for you!”
She shook some more powder between my legs where the plastic might rub and then began putting my shoes on.
“B-b-but, can’t I wear my pants please?” I quailed.
“These will be just fine,” she said as she patted the now thick crotch of my waterproof panties, “besides, you’d never be able to get your pants over these diapers anyway.”
I bunched my fists in mute helplessness and fought back tears of humiliation.
“It’s not fair!” I pouted.
“Now don’t you worry about a thing. In half an hour, you will have forgotten all about your diapers,” she assured me as finished tying my shoes, “but if you have to go potty, you be sure to tell me, okay Honey?”
I nodded my head but my cheeks buzzed with shame. I hadn’t worn diapers for five years now and it was utterly humiliating to have to wear them now.
As I got off of the bed, I felt the slippery plastic between my legs as they rubbed against the thick material. With only a t-shirt on, the fat diaper made me look like a two year old toddler and thats exactly what I felt like as I waddled out of the room. I passed by the bathroom and I couldn’t help but look at myself in the full view mirror there. The colorful nursery characters decorating my plastic pants seemed to be shouting what a big baby I was and my bottom bulged roundly. I hurried away from the humiliating reflection as fast as I could.
Going out into the living room, I turned on the tv to see what was on.
“Why don’t you go outside and play?” Vanessa suggested.
“No thanks,” I mumbled. The last thing I needed was for anyone else to see me dressed up like this. I was determined to do whatever was necessary to keep my diapers dry and get out of them as soon as possible.
Before long, I was absorbed in a show on tv and I tuned out the rest of the world. So much so, that I didn’t see or hear the people coming up the front sidewalk that went along the front window. I was lying down on my stomach, my head propped on my hands watching the tv when the group opened the door unannounced.
“Vanessa! We’re here!” an older woman’s voice said.
Behind her were two young girls about my age or a little older, and when they walked in and caught sight of me, they broke into gales of laughter.
I gasped and blushed beet red, jumping to my feet in horror. This was the worst possible thing that could happen! I recognized the girls from my school. I had always thought they were really cute but they had never deigned to talk to me and now here they were, staring at me and laughing out loud. In a state of panic, I tried to bolt out of the room but instead, I ran headlong into Vanessa. She blocked my way and prevented me from escaping as she took hold of my wrist and turned me around to face her guests.
“Jimmy, don’t be so rude. Say hi to our friends,” she insisted.
I struggled weakly as my face turned a bright shade of red.
“Well, it looks like someone has been very well diapered,” their mom said approvingly.
“Yes, I didn’t want a repeat of last week’s little incident,” Vanessa told her.
“Well, these should take care of that, shouldn’t they, Young Man?” she said as she reached down and patted me on the thick seat of my diaper.
I was speechless as I stood there, helpless to get away from them.
“Jimmy, I think you know Tammy and Brittany from school?” Vanessa asked sweetly.
I nodded my head in shame.
“Girls, this is Jimmy. Now I want you all to get along while your mother’s out shopping, okay?” she said.
“Yes Ma’am,” they said in unison as they stifled some more giggles.
“That’s it girls,” their mom said pleased, “And don’t you worry Jimmy,” she said as she held my chin up to look me in the eyes, “some little boys take longer than others to grow out of diapers. And some boys just never seem to outgrow them.
“I’m sure you three will have a wonderful afternoon together.”
I fidgeted nervously as they said their goodbyes and the mother departed. Almost immediately, Tammy and Brittany began whispering to each other and I knew it could only be about me.
“Come on Baby, you can play house with us,” the latter said with a snicker.
“My name’s Jim!” I said hotly, “And I don’t wanna play any dumb house with you.”
“Temper, temper, Baby,” Tammy said, wagging a finger at me, “better not get snotty with us or we’ll tell everyone at school what you’re wearing now.”
A new shiver of fear ran through me as I imagined what my friends would say if they heard I was wearing diapers again.
I had had a long and difficult time getting potty trained, much to my mom’s chagrin and frustration. I was four by the time I graduated to training panties and another long year before I was finally able to go to bed without being pinned into a thick diapers and plastic pants to protect my bed at night. I still had the occasional dribble or accident before I reached the bathroom but nothing too often or too much for my mom to put me back into diapers.
“Please don’t!” I begged suddenly, my earlier bluster gone, “please don’t tell anyone.”
“Then you better do as we tell you…Baby,” Brittany said ominously.
We went into the back yard which thankfully, was fenced off from the rest of the neighborhood. However, that didn’t prevent me from looking around every five minutes just to make sure no one was looking over the edges.
I played along with the girls reluctantly and hoped by cooperating that they’d keep my diapers a secret. They teased me mercilessly, calling me a little sissy baby and a potty pants but I had no choice but to tolerate their treatment.
At one point, we got into a bit of a tussle and I found myself wrestling with the two girls. I had to admit, I felt pretty lucky to be in such close contact with these cuties that otherwise never would have given me the time of day back at school. But things took a turn for the worse when they held me down and started tickling me. I begged them to let me up but they were much too strong for me. I giggled hysterically until the inevitable happened. Kicking my feet into the air as I struggled, I proceeded to pee uncontrollably into my diapers. I think they sensed what was happening because they kept on tickling me until I had thoroughly soaked myself.
When they let me up, I looked down at the huge wet spot in the front of my diaper and my laughter turned into tears.
Just then, Vanessa appeared at the back door to investigate.
“What’s going on out here?” she inquired.
The girls just looked at each other and smiled while I sobbed in shame.
Vanessa came over and looked down at my diapers, instantly realizing what had happened.
“Shhh…don’t you worry Jimmy, we’ll get you into some fresh dry diapers right away,” she said as she hugged me to her big, soft bosom.
“B-but, they made me do it,” I cried in despair.
“Shhh,” she said shushing me, “it’s okay Jimmy. It’s like Mrs. Turner said, some little boys just need their diapers a little longer than others. Come on inside and we’ll get you all fixed up.”
Everyone went inside and we went back into the bedroom where I was first diapered.
“What about them?” I protested as I saw Vanessa wasn’t making any attempt to exclude them from watching.
“Hush Baby,” she said without answering me.
She unfolded a changing pad and placed it on the bed, sitting me on top of it. If I was embarrassed before, this was twice as bad as Vanessa peeled the clinging plastic pants off of my diaper and down my legs. The girls watched with amusement as she unpinned my wet diaper and pulled it out from under me, dropping it into a nearby diaper pail. I turned my head away from the girls as she began meticulously wiping my crotch and bottom with cool baby wipes. After powdering me and smoothing it onto my bottom and tiny penis, she began gathering a new stack of diapers to put on me.
“Please, please can’t I go without diapers Ma’am?” I pleaded strenuously.
“I’m afraid not Jimmy. You’ve shown me very plainly that you can’t be trusted without them,” she explained, “and after this it’ll be naptime and I don’t want you wetting my bed.
“Just in case, I think I better add a soaker pad since you seem to be a heavy wetter.”
I cried softly as she lifted up my bottom and slid the thick diapers underneath me. More powder followed and she re-pinned the sides, locking me securely into my baby soft prison once again.
“Here’s some plastic panties for him,” Tammy offered, a little too helpfully, as she held out a pair of pink nursery print vinyl panties.
“Thank you Tammy,” Vanessa told her, as she took them and began sliding them up my legs.
I resisted her efforts, thrashing my legs in protest.
“But those are for girls!” I complained.
“Now Jimmy. I don’t have a lot of plastic panties for you to choose from. You’ll just have to wear what I have available,” she said tugging them up and into place.
“It’s not fair,” I pouted, “it’s not fair.”
“Shu-shush, Little Baby,” she said trying to sooth me.
These diapers were even bulkier than the last set I was wearing and they billowed out from my skinny body in the most humiliating way.
“There you go. All safe and secure!” Vanessa enthused as she snapped the elastic waistband of my panties.
Tammy and Brittany giggled at my predicament and I felt my eyes filling with tears.
“And now it’s naptime for my little one,” she said as she put the diapering supplies away.
“But I never take naps!” I whined bitterly.
“Well you do in this house,” she said firmly, “and I’ve had just about enough of that attitude Young Man. You’d better work on your manners or you’ll find yourself over my lap in no time.”
I gulped in fear but said nothing as she led me down the hallway to another room. It looked like a little girl’s room with frilly curtains and pink furniture and she closed the curtains before sitting me on the bed. My thick diapers caused me to sit a little higher than I would normally and Vanessa untied my shoes while I gazed down the front of her top. I could easily see the soft, smooth skin of her breasts where they curved together and formed a deep cleavage, her lacey bra peeking out from the low cut of her top.
She pulled back the covers and tucked me in, handing me a teddy bear to console me.
“That’ll make you feel better, Honey,” she said as she draped my arm over it.
Walking out of the room, I watched the light play on her long, silky legs as she went out the doorway.
For the first time since my traumatic morning began, I was alone.
My hands went down to touch the soft vinyl of my plastic panties. My diaper felt very cushiony and it occurred to me that they were far more pleasing against my skin than my normal underwear. I had forgotten how soft cloth diapers were and I blushed at the realization of it.
Somehow, I drifted off to sleep, hearing voices down the hall and wondering why the girls didn’t have to take a nap like me…

I woke up to the feeling of my bottom being squeezed by Vanessa’s hand. For a moment, I forgot where I was and in a panic, I jerked away and sat up.
“Mommy!” I cried.
In the darkness of the room, I heard the unmistakable sound of Tammy and Brittany’s giggling and I remembered where I was.
“Jimmy. Have you wet your diapers again?” Vanessa asked incredulously.
“Uh-uh!” I denied emphatically but as I sat here on the bed, I knew with certainty that I was soaking wet. How did THAT happen? I almost never wet the bed, I thought frantically. I blushed in shame as the girls whispered amongst each other and giggled some more.
Vanessa stood there with her hands on her curvy hips, framed in the light from the door staring down at me.
“You really ARE a big baby, aren’t you?” she said, her voice filled with disbelief and disappointment.
“I don’t know what happened!” I cried, “honest!”
She shook her head and frowned down at me but said nothing.
“Come along, Jimmy,” she said with a heavy sigh, “time to change your diapers…again!”
I followed her out, accompanied by the whispers and snickering of the other two girls. Somehow, I wondered if they had done something to me while I was asleep.
“Honestly, I don’t know how your mother ever graduated you out of diapers,” Vanessa said as she placed me back on the changing pad.
“But I never pee my pants at home!” I said defensively.
“Oh, and you only do it when you’re being babysat then?” she asked pointedly.
“No!” I cried, but she was already peeling my plastic panties down again.
“Well I’m going to tell her you belong back in diapers, full time. I’ve never seen someone with a wetting problem like yours and I’ve babysat a lot of little boys. You should be ashamed!” she scolded me as she gave my bottom a stinging slap.
I cried tears of humiliation as she pinned me back into another set of thick, thirsty diapers, covering them again with a frilly pair of pink plastic panties with snaps on the sides.
Just then, the doorbell rang and I held my breath in nervous anticipation.
“You come along where I can keep an eye on you,” she said firmly.
Vanessa took a firm hold of my wrist, pulling me along behind her and I waddled as best I could. The thickness of these diapers made normal walking impossible but I also found that the soft ruffles around the panty legs kind of tickled my inner thighs.
Doing everything I could to hide behind Vanessa, I swallowed hard as she answered the door.
“Hello!” she said as she greeted my mom.
My face turned a bright shade of red as she spied me fidgeting behind my sexy babysitter.
“Jimmy? What happened to your pants?” she demanded suddenly.
“I think you’d better come inside,” Vanessa told her.
My mom fixed me with a hard look and I bit on my lip nervously. This was not going to look good for me and I racked my mind for a suitable explanation that would help me avoid the inevitable punishment.
“Lately, I been having to take ‘precautions’ for some of the little boys who stay over here,” Vanessa began, ”there have been some wetting incidents from some of them that I had been led to understand were already potty trained.”
My mom listened in silence while I looked at the ground, praying it would open up and swallow me. I was for sure going to be in serious trouble when my mom found out what I’d done today and my bottom twitched nervously.
“Apparently little Jimmy here has a wetting problem because I’ve already had to change him twice today.
“If I were you, I would strongly consider putting him back into diapers full time,” she finished.
My mom regarded me darkly with a mixture of anger and disgust.
“Jimmy? You are in big trouble Young Man. What do you have to say for yourself?” she demanded.
As I stood there, quivering in fear, dressed only in my sneakers, t-shirt, and a thick diaper and frilly plastic panties, Tammy and Brittany showed up to witness what was happening.
“I-I-um, I just…um…” I stammered foolishly. I couldn’t think of anything to get me out of this situation.
“Jimmy–you should be ashamed of yourself!” she snapped, cutting me off sharply.
I fidgeted in front of everyone, shifting from one foot to another as I kept my crimson face downcast. I could feel the heat all the way to my ears and I knew my neck was flushed as well.
My only hope was to stall until we got home, maybe then I could hope to explain my way out of a spanking.
“So help me, if I had a paddle here…” she said menacingly.
“Maybe I can help you,” Vanessa offered brightly.
Stepping out of the living room, she disappeared down the hall, only to return a moment later. In her hand, she was carrying an oval wooden paddle, with a double row of small holes in its face. My heart skipped a beat and my eyes went wide as she handed it to my grateful mother. I licked my dry lips as she fixed me with her determined stare.
“No mommy-please!” I begged her abjectly.
Ignoring my plea, she reached down and snatched my wrist, yanking me over to the couch. My legs felt like rubber and I whimpered in fear as she took a seat. In my heightened state of anxiety, I felt a trickle of pee escape into my diapers before I could prevent it.
“Oh!” I squealed.
My hands shot down to the front of my diapers and I crossed my legs in futility. Crocodile tears filled my eyes and I tried weakly to stop her from pulling my diapers down.
“Nooo! Please Mommy! It was an accident!” I cried.
“What did I tell you was going to happen if you wet your pants again?” she said as she brusquely slapped my hands out of the way.
“I-I-I’d g-get a sp-spanking,” I sobbed pitifully.
“Thats right Jimmy. A spanking, And now I’m going to blister your bottom.”
Throwing me across her lap, she surprised me by leaving my diapers in place. Maybe she intended to just give me a demonstration of her anger by spanking me on my well padded fanny. If that were the case, all I’d have to do was to cry some more fake tears for show, and then it’d be all over.
My short lived sense of reprieve was not to be however–instead, as I lay face downwards with my diapered bottom up in the air, she gripped the elastic waistband of my plastic panties and yanked downward, unsnapping the side snaps in one swift move. Pushing the back of my panties out of the way, she proceeded to unpin the thick cloth of my diapers and push that back as well.
Now my tender bottom lay exposed to everyone and I saw Brittany smiling at me wickedly.
“Mommy nooo!” I wailed but I was cut short by the stinging slap of the paddle.
“OWWW-WAA!!!” I cried.
The paddle rained down on my youthful cheeks harshly, searing them in a merciless rhythm of retribution. I kicked and sobbed, banging the floor with my hands and wriggling over her lap in a futile attempt to escape. My mom was quite strong however and I was no match for her. She easily held me in place while she paddled my bottom determinedly.
I cried for all I was worth as the assault on my fanny continued. My mom delivered harsh, angry swats with the paddle, starting first with the center of my rump, and then steadily working her way outward, so that the sides of my cheeks received equal punishment. They went from a bright, candy apple red, to a flaming, deep crimson, hot and stinging over every square inch.
At long last, the spanking was over.
I lay over her lap, too weak to move, bawling like a baby. I knew I was making a spectacle of myself in front of all these people but I couldn’t help myself. As I cried, I felt my mom pulling the sides of my diaper together and pin them closed. Apparently I was going to have to wear them home, although at this moment, I no longer cared.
Taking the back of my plastic panties, she pulled them up and began snapping the individual side snaps. This effectively sealed in the blazing heat on my bottom, causing me to burst into a fresh set of tears.
With little sympathy, my mom raised me up into a standing position and I rubbed the soft, ruffled seat of my diapers desperately, trying to assuage the pain. At the same time, my legs were wobbly and unsteady and my sobbing went unabated.
”Jimmy, since you’ve demonstrated that you can’t be trusted without wearing diapers, you can just wear these home,” my mom instructed me.
“Y-yes Mommy,” I cried through my tears.
“But on the way, we’re going to stop by the store and get your own supply. From now on, you are going to be wearing diapers full time, until you can prove to me that you’ve grown up enough to go without them. Do I make myself clear?”
“Yes M-mommy,” I responded abjectly.
“Now I want you to thank Miss Vanessa for taking care of you while I was gone,” she ordered me.
“Tha-thank you, Miss Vanessa,” I sniffled between my sobs.
“And thank her for having the foresight to put you back into diapers where you belong.”
I had never been so humiliated in my entire life but after that spanking, I was completely defeated.
“Th-thank you for…for putting me in…d-diapers,” I mumbled.
“I don’t think she heard you Jimmy,” my mom said as she crossed her arms over her chest.
I cleared my throat nervously, blushing again.
“Thank you for putting me back in d-diapers, Miss Vanessa,” I repeated, my face turning a fresh shade of red.
“You’re quite welcome, Sweety,” she said pleasantly, ”you can be my little baby anytime you want. Maybe next time, we can find a cute little outfit for you to wear.”
That last comment brought a round of giggles from Tammy and Brittany which caused me to lower my gaze in embarrassment.
“Well come along, Jimmy. It’s time to go now. Say goodbye to your little friends here,” my mom instructed me.
”Bye,” I said, barely audible.
“Bye Jimmy,” they sang in unison with big smiles on their faces.
My mom returned the paddle back to Vanessa on our way out in exchange for my folded pair of jeans.
“Thank you again for everything,” she said to her.
“No problem at all,” she replied, ”good luck with your potty training, Jimmy.”
I waddled out to the car miserably and sat down, wincing as my fanny came into contact with the seat. My mom got in behind the steering wheel and started the car.
“When you get home, the first thing I want you to do is to go to your room and box up all your old underwear. Do you understand me?” she asked.
“Yes Mommy,” I said meekly. I knew better than to argue with her now since I didn’t want another session with the paddle she kept at home.
“From now on, these will be all the underwear you require,” she said as she patted the plastic covered front of my diapers.
I sniffled abjectly as I shifted in my seat, trying to find a position that wasn’t so painful for my punished bottom.
We drove down to a store nearby our house that until now, I’d never paid any attention to as it was devoted to babies. When we pulled up, I looked with feelings of dread and fear at the displays of baby furniture in the windows.
As my mom shut off the engine, she got out and waited for me to follow but I was frozen in my seat.
“Mom…can’t I just stay in the car?” I pleaded.
“Young Man, you get out of that car this instant. If you didn’t want people to see you in diapers, you should have thought about that before you started wetting them like a little baby,” she told me in her no nonsense tone.
With great reluctance, I stepped gingerly out of the car, moving towards her hesitantly.
“Come on Jimmy, we haven’t got all day,” she snapped impatiently.
Pouting helplessly, I trudged behind her and we entered the store.
It was like a giant department store for babies and toddlers and I felt very subconscious at my advanced age of ten. She pulled me along like a small child behind her and we went down the aisles toward the diaper section. We passed several mothers and their children and without exception, they looked me up and down thoroughly, some of them shaking their heads before moving on.
When we reached the diaper section, my mom began sifting through the various types trying to find the ones she wanted. From behind me, I heard a woman’s voice and it caught me by surprise.
“Is there anything I can help you with?” she asked.
Turning to face her, I saw she was a pretty woman in her late twenties, with long curly blond hair, and a generous bosom. I blushed deeply as she bent down to take a closer look at me and her beautiful smile only made me more uncomfortable. Her tight yellow halter clung deliciously to her big breasts and I stared at their perfect curves with my mouth open.
“Yes, maybe you can,” my mom replied, ”My little Jimmy here has a wetting problem and has to wear diapers. Can you recommend any that would fit him?”
For a brief nanosecond, I held out the hope that she’d say no but then once again, my hopes were summarily dashed.
“Oh yes!” she exclaimed, ”we have all kinds of diapers to fit your little boy.”
My heart sank upon hearing that and I reluctantly followed them down the aisle about ten feet. Once there, the pretty saleswoman showed my mom several different types of cloth and disposable diapers, all cut generously to fit bigger boys like me. My mom held up a thick disposable that were made by Pampers, noting how crinkly they were.
“Do you think these will be heard under his regular pants?” she inquired.
“I’m afraid so,” the woman admitted, her smooth brow creasing slightly.
“Well, you’ll just have to get used to it Jimmy,” my mom told me.
After getting several armloads of both types of diapers, we went over to the plastic panty section. I was starting to feel the beginnings of the need to pee and I hoped this wouldn’t take much longer. My bladder control had never been very strong and I worried how long I’d be able to hold out.
My mom and the lady talked for what seemed like forever on the benefits of the various types of rubber and plastic panties, which of them were most comfortable for long term wearing, which were the most leak proof, how best to wash them, and so on. All this talk about wetting made me have to go all the more and I became impatient to leave. I danced around next to them counting the seconds and straining my pee-pee to hold back the tide. I also tried to distract myself by watching the saleslady before me. I noticed that every time she breathed, the smooth, exposed tops of her breasts would rise and fall erotically and they jiggled as she moved about. They reminded me of two big grapefruits, perfectly round and barely contained within her top. At one point, she accidentally bumped into me and my heart skipped a beat as her big soft breast mashed against my face.
I blushed again but she smiled down at me knowingly.
After my mom had picked up numerous pairs of plastic panties, we finally headed to the checkout counter. I had to stand in line with a number of other people, all of whom stared at my exposed diapers and bare legs. I bit my lip in frustration as a woman in front of us was conducting a return transaction, bringing our progress to a crawl.
By now, the pressure on my bladder was growing ever greater and I shifted back and forth trying to hold it in. It didn’t help things that there was a damp spot already in the front of my diapers and I began to seriously doubt whether I’d be able to hold it until I got home.
“Mommy,” I said urgently tugging on her sleeve, ”I gotta go pee!”
My mom gave me an annoyed look and she frowned down at me.
“You’ll just have to wait until we get home,” she said curtly, ”try to control yourself.”
I bit my lip again as I strained against the growing urge. Suddenly, from behind me, I felt the thick seat of my diapers being squeezed. Turning around, I blushed red as I saw an older woman smiling broadly down at me.
“You remind me of my own grandson,” she said warmly, ”he wore baby diapers until he was seven.”
My face burned from embarrassment but I said nothing.
“How old are you, little boy?” she asked nicely.
“Ten and a half,” I mumbled, instantly regretting the latter embellishment.
“My, you’re a little old to still be wearing diapers, aren’t you?” she asked surprised.
“Yes Ma’am,” I murmured, my ears starting to warm as well. By now, the ladies behind her had taken an interest in our conversation and they listened and watched me closely.
Hoping to put an end to this humiliation as quickly as possible, I spun around and faced forward, trying to block them out and concentrate on not wetting myself any further.
The lady behind me patted my ruffled bottom gently and bent down to whisper in my ear.
“Don’t worry Honey, some little boys never outgrow their diapers. But you look very cute in yours.”
My eyes filled with tears as I endured the intense humiliation. Worse yet, my bladder felt ready to explode. As we finally got to the checkout stand and my mom was placing the diapers and plastic panties on the counter, I shook her sleeve frantically.
“Mommy, I gotta go!” I pleaded piteously.
“Jimmy! Control yourself!” she replied angrily.
I let out a whimper and the floodgates opened. With a sob of despair, I proceeded to flood my diapers, the warm streams of pee coming one right after another. I balled my hands into fists and shook them impotently while I stood, helplessly wetting myself like a two year old toddler in front of everyone. Soaking them thoroughly, my diapers grew heavy and began to sag. The warm wetness seeped back, saturating my crotch and then between my legs as the last stream finally reduced to a trickle.
The lady behind me bent down and patted my warm bottom tenderly.
“It’s okay Baby, let it all out.”
The humiliation was too much for me and I burst into tears. My mom looked down at me and sighed heavily. The lady behind me dug in her purse and produced a large pink pacifier, holding it in front of my quivering mouth.
“Aww, poor thing, would you like a paci to sooth you?” she asked sweetly.
I shook my head no but my mom took the pacifier and coaxed it into my mouth where I was forced to suck on it. A couple of younger women behind us giggled at the sight of my infantile appearance which did nothing to help my disposition. In a fit of sissyish frustration, I stamped my feet and threw a tantrum.
My mom ignored me but thanked the lady behind us and then, noticing my diapers sagging lower, she reached down and tugged them upwards by the waistband. The wet, pee soaked cloth embraced me closely, hugging my bottom and groin areas in a constant reminder of my babyishness.
After paying for our items, we finally left the store but not before the lady behind me gave my seat a playful slap. It landed with a distinctive sound of a firm maternal hand striking thickly padded vinyl panties.
“Bye-bye Sweetie-pie,” she called out to me.
I was vastly relieved to escape that store – I had never experienced anything so humiliating in my entire life.
The ride home was silent and I knew my mom was still upset with me. My bottom remained sore from my earlier spanking but by now the wetness had seeped back and was covering my tender cheeks. With my snug plastic panties, there was no escaping the warm wetness that clung stubbornly to my skin.
When I got home, we both went to my bedroom together. As my mom began making space for the stacks of cloth diapers she’d purchased, I stood in such a way as to minimize my skin contact with the wet cloth I was wearing.
“Mom? Can I please get changed now?” I begged her.
“Not yet Jimmy. I want you to go out to the garage and get a box for your old underwear,” she told me.
“But how long am I gonna have to wear diapers?” I complained.
“As long as you insist on acting like a baby, that’s how long,” she retorted.
Glumly, I trudged out and got the box, still unaccustomed to the feeling of wearing a warm, wet diaper that I couldn’t ignore.
When I returned to the bedroom, I was surprised to see that my mom had set up an extensive diapering area. On my desser, she had cleared away all my model airplanes and pictures. In their place were baby powder, diaper pins, baby wipes, and diaper rash creme.
Wordlessly, I began gathering my underwear and dumping it in the cardboard box as my mom filled the drawer with various plastic panties. She had chosen several different types, both pull up and sidesnap and all in childish pastel colors of white, yellow and baby blue. Removing a pair of the yellow ones, she laid them next to a vinyl changing pad that was spread across the bed. I grimaced as I looked at the nursery characters decorating the pad and taking my hand, she sat me down on it where I landed with a wet squish. Putting her fingers inside the elastic waistband of my plastic panties, she peeled them down off the sopping wet cloth and pulled them down my legs. Unpinning my diapers, she tugged them out from under me and dropped them into a plastic pail.
After getting several baby wipes, she cleaned my bottom and private area thoroughly, before getting the jar of diaper rash creme. With three fingers, she took a good sized glob of the creme and as she lifted me up by my feet, she proceeded to slather my still pink bottom with a thick coating of the substance. I blushed anew at this distinctively babyish procedure which was further enhanced by the nursery print that surrounded me on my new changing pad and the smell of the nearby vinyl. However, for the first time since we’d left Vanessa’s house, my bottom was finally getting some relief and the cool diaper rash creme soothed the residual stinging on my tender fanny.
“I’m sorry I had to spank you Jimmy,” my mom said, as her hand gently spread the creme over the surface of my buns, ”but you really disappointed me today.”
“Yes Mommy,” I said, happy to see her change of demeanor.
“I thought we were all done with your potty training when you got into kindergarden, but now it seems like we’re right back where we started.”
“I’m sorry Mommy. I promise to do better from now on,” I told her hopefully.
“Hmmph. I doubt that,” she said skeptically, ” I think you’ll be wearing diapers and plastic panties for a long time to come.”
If only I had known how true her words would turn out to be…
Taking three of the pre-formed diapers, she slide them under my now shimmering rump, situating them until they were even on both sides. Then she shook baby powder over my privates and between my legs, even lifting up my tiny pee-pee to powder there. When she was done, a cloud had risen around me and the unmistakable infantile scent filled the room.
She pulled the diapers up between my legs and pinned each side closed securely while I looked away in embarrassment. Taking the yellow pair of plastic panties, she removed the cardboard label and shook them out, gathering the leg holes together in her hands.
“Feet up,” she ordered me tersely.
I did as I was told and she pulled the soft plastic panties down my legs to the base of my thighs. It took a little effort to manuever the panties up and over my bulging diapers but by running her fingers back and forth around the waistband, she worked them up and over until the cloth was completely encased. My mom was nothing if not thorough and she ran her fingers around the leg and waistbands, making sure the diapers were completely contained. That done, she pushed my legs apart and powdered between them generously to prevent chafe.
“There you are Jimmy. That should last you until bedtime.”
I blushed again at her appraisal which showed how little confidence she had that I’d be able to stay dry anymore.
Sliding off the bed, I waddled out of the room, extremely concious of the soft, but bulky diapers I was now permanently imprisoned in. It was a feeling I would come to be intimately familiar with.

A week and a half later, I was no closer to getting out of diapers and back into my regular underwear. Even though I hadn’t had any major accidents or anything, I occasionally would have “dribbles” or wet spots, where I didn’t quite get to the bathroom on time. And my mom never made any mention of letting me wear regular underwear, despite what I thought had been a pretty good record.
On one day, she had to go in town for a long meeting and she dropped me off once again at Vanessa’s house. When I arrived, my earlier nemesis, Brittany, was already there and my heart sank. I was wearing my usual outfit for these days, a t-shirt, sneakers, and by now, the mandatory exposed diapers and plastic panties.
Vanessa looked as stunning as she was the first time I met her, even though she was only wearing a very simple outfit. She had on a short pink skirt which showed off her fabulous legs and thighs to great effect. However, it was the top she was wearing that I couldn’t take my eyes off of. It was a thin, tight white material that wrapped across her unbelievable bosom diagonally from either side, resulting in a plunging V that displayed her deep cleavage that couldn’t be ignored.
“Well, it looks like your mommy decided to keep you in diapers after all, Jimmy,” she said brightly.
I nodded in embarassment and she patted my thick seat appreciatively.
“I guess I better make sure I’ve got plenty of spares if you plan on wetting them like you did last time you were here,” she said, bending down to speak to me.
I remained mute as I gaped openly at her mouth watering breasts, hanging before my face with perfect form and roundness.
As soon as we were alone, Brittany wasted no time in teasing me mercilessly. She compared me to her little brother, a toddler of four who was just graduating to training pants.
“Maybe someday YOU can wear training pants, Sissy,” she derided me.
I was forced to endure her insults as best I could since she still held the power over me of revealing my secret to everyone else. The problem was, she seemed to be using that power to greater and greater effect to dominate me. She decided we were going to play house again but this time, I was going to be her baby girl. I resisted strenuously until we got in a scuffle. I had never been known for my fighting prowess and as it turned out, despite the fact that I was larger in size, she had me down on the ground with my arm twisted behind my back in a matter of seconds. She made me say all kinds of humiliating things but the worst was having to beg to wear a dress. She made me promise to repeat myself to Vanessa or else she’d really make me sorry.
Being rather meek by nature, I reluctantly agreed and we went inside to find Vanessa. Brittany instructed me to let her do most of the talking and we found Vanessa filing her nails.
“Aunt Vanessa? We wanted to play house outside and Jimmy wants to be my little girl. Do you think you might have anything that he could wear?” she asked.
“Well,” Vanessa said, clearly interested, ”I’m sure I can find something cute for him to try on. My niece stays here from time to time and I think I have one of her Sunday school dresses in the other room.”
I followed them down the hall with leaden feet as Vanessa went to retrieve the clothes. Sorting through a closet, she produced a pink and white taffeta dress, very fancy, with miles of frills and lace. As Brittany giggled with delight, I groaned in helpless frustration as this instrument of my humiliation was held in front of me.
“Well, it looks like it may be a bit short but you don’t mind that, do you Jimmy?” she asked me.
I was about to blurt out that I very much did mind but I felt Brittany step on my toe painfully.
“Ouch! …No Ma’am…i-it’s okay,” I mumbled, cursing myself for my weakness and lack of will.
Removing my t-shirt, she threw it on the bed and then instructed me to lift my arms up. She lowered the lacey confection over my head and adjusted the puffy short sleeves and hem which only just covered the elastic waistband of my plastic panties. I tugged at it myself to help but it was obvious that no effort was going to make it cover any more of my bulging diapers than the top inch or so. Under the dress was a petticoat of sorts, that flared the dress outwards with row upon row of white, pretty ruffled lace. Turning me around, she buttoned up the dress in back all the way to the neckline, effectively securing me into the babyish outfit.
Vanessa smiled down at me and saw me tugging at the hem in frustration.
“Aww…you’d like something else to cover your diapers wouldn’t you?” she asked me gently.
“Yes Ma’am,” I quickly agreed. Maybe she’d forget about this dumb dress and let me go back to wearing my t-shirt. Instead, she dug in a drawer until she found a silky pair of pink rhumba panties, with three rows of big ruffles gracing the seat.
“Here you are Sweety!” she said, obviously very pleased.
I stamped my feet and gritted my teeth as she snaked the stretchy panties up my legs and over my thick diaper. Afterwards, she fluffed the hem of my dress all around, making sure it wasn’t tucked in anywhere.
“Oh, don’t you look darling,” she said admiringly.
I blushed as I looked down at my sissyish appearance. The thing is, the dress had a strange effect on me, making me feel even more effeminate and babyish. It was like Vanessa was reading my mind because she snapped her fingers and turned around, getting something from behind her.
“I know! I have just the thing!” she said as she popped a big pink pacifier in my mouth.
I sucked helpelessly as my eyes brimmed with tears of shame. Vanessa must have noticed because her smile briefly disappeared.
“What’s the matter Honey? Have you wet yourself?” she asked, immediately checking at the legbands of my diapers.
I shook my head no and pouted in front of her like a toddler.
“Well if you do, you just tell Brittany and we’ll make sure to get you changed you right away…okay Honey?” she said ever so sweetly.
I nodded my head and sniffed as I looked down at the floor.
“Come on Baby,” Brittany said with a broad grin, as she took my hand and pulled me out of the room.
A moment later, we were outside again in Vanessa’s sunny backyard. Brittany sat me at her tea table and made me talk like a baby with her, after which she filled a bottle with warm milk and instructed me finish it. In my diapers and frilly dress, I couldn’t help but feel like a little baby and I found myself thinking less and less like a big boy of ten and a half. Without thinking, I nearly wet myself and I only caught it, just in the nick of time. My mom only needed the slightest excuse to extend my diaper treatment and if she found out I’d wet another pair, she’d be sure to forget any plans for potty training me.
After about an hour, we heard the voice of Brittany’s mother calling her from inside the house. I would of course, have preferred to stay where I was but Brittany insisted on forceably pulling me by my wrist back inside.
When her mom spied me in my sissyish outfit, she giggled and smiled down at me, looking me up and down in an appraising manner.
“Yes…oh yes. That definately suits you,” she said enthusiastically. Walking around to where she could see my behind, she nodded her head up and down agreeably, “oh yes, you should have been born a girl, Jimmy. That dress looks just right on you.”
I blushed hotly under her examination and comments, unable to form a reply.
“Where did you find it?” she asked Vanessa who was also smiling down at me.
“I was fortunate to have a few outfits left over from when Janie was here last month,” she explained happily.
“Well, it seems so appropriate for someone like him, an obvious sissy who still needs his diapers.”
I tried desperately to fight back the tears from this humiliating assault but I didn’t want to appear more like a baby than I already was.
“Now all you need are some lacey anklets and mary jane shoes, Jimmy,” she said as she adjusted the short puff sleeves of my dress.
They finally said their goodbyes, much to my relief, and I was left alone to amuse myself as I saw fit. Even though Brittany was gone and I was no longer obligated to “play house”, Vanessa left me as I was dressed, and she went back to whatever she was doing previously.
At one point, I wandered into the bathroom where a full length mirror stood on the wall. A strange part of me was curious to look at the way I appeared and after making sure Vanessa wasn’t around, I gazed at my reflection in the mirror. My sneakers gave me a boyish look but that was where it ended. When I looked at the white ruffled edges of my pink rhumba panties, my face reddened and grew redder as I twirled around to see the bouncy rows of ruffles across my big, round, diapered bottom. The frilly dress I was wearing made me feel girlish and I felt an odd sensation inside that I couldn’t quite explain. Part of me wanted to admit that secretly, maybe I was just a big sissy, who needed to be dressed in diapers and little girl’s clothes. I shuddered to myself at the realization but quickly rejected it.
Suddenly, I heard Vanessa call my name from down the hall and I wondered to myself what further torments she had in mind. Waddling down the hall, I made my way into her bedroom, which was softly lit and very feminine. She had an ornate four poster bed with frilly curtains that adorned the corners and the rest of the room’s appointments reflected her sexy personality.
I saw her sitting on the bed, looking relaxed with a couple of fluffy pillows propped up behind her back. I couldn’t help but notice that the warm lighting only enhanced her fabulous figure, creating deep shadows between her fabulous breasts.
“Come over here and sit next to me, Jimmy,” she said, beckoning me as she patted the bed. I found it difficult to hold the gaze of her beguiling eyes because of my shyness, but I moved closer and worked my way onto the bed.
Vanessa had a devastating smile and when she graced me with it, I nearly fainted. Taking me by the hand, she pulled me up between her long, smooth thighs and fixed me with a seductive look that made me quiver.
“You know, in my house, naughty little boys get spanked…” she said, her voice silky and disarming.
“Um…uh-huh,” I said uncertainly, suddenly becoming very nervous.
“But good little boys get treats,” she continued, her beautiful smile washing over me like a warm wave.
Her perfectly manicured hands moved to her immense bosom, stroking and cupping her breasts in a very inviting manner.
“I’ve noticed you staring at my boobs, Jimmy, maybe you’d like to take a closer look, hmm?”
My heart was beating wildly now in this intimate setting and I felt a strange but pleasant sensation in my groin as I stared openly at my sexy babysitter fondling her massive breasts. Each one looked about the size of my head and I found my breath coming in short gasps as I tried to come to grips with what was happening.
Slowly and teasingly, she slid back the thin material of one side of her top, exposing the white lacey bra that barely held her tremendous breast. I licked my dry lips, unable to take my eyes off her smooth, curvacious skin. I watched her long french nails as she pinched the firm nipple through the fabric of her bra, causing it to protrude even more enticingly.
Vanessa put her other hand on my head and gently pulled me toward her chest. At the same time, she pulled her big breast out of the cup of her bra and offered it before my quivering lips. Like a starving boy, I closed my mouth over her nipple, the flesh warm and delightful in my mouth. My nostrils were filled with the wonderful scent of her skin as well as a slight trace of her perfume and my head swam with ectasy.
“That’s it, Little Baby,” she said softly as she caressed the top of my head, ”nurse from mommy’s boobs.”
Within the warm folds of my thick diaper, I felt my tiny pee-wee straining against it’s bunny soft confines and I sucked greedily on the hard nipple filling my mouth. I was in state of unbridled pleasure as I felt Vanessa’s hand move down to the front of my diaper and begin stroking it softly. My breath was coming in gasps as I sucked like an infant. My forward vision was filled with her incredible breast and out of the corner of my eye, I could see across her deep cleavage, where her other boob was still confined within the cup of her lacey bra. The combination of sensations and sights was too much for my juvenile composure and I suddenly experienced my first orgasm, blinding in it’s power and scope. I whimpered and gasped as my head spun and my vision swam. I had never experienced ANYTHING like this in my entire ten years of existence.
I sat back, breathing hard as my heart raced and my vision began to return, my mind still trying to undertand what just happened.
“Did my little baby like that?” Vanessa whispered softly in my ear.
I nodded enthusiastically, still unable to speak as I tried to catch my breath.
Vanessa gazed down at me with that devastating smile as she placed her breast back within the cup of her bra and returned her top to its original position.
“And now I want you to do me a favor,” she said sweetly.
At that moment, I would have chopped my arm off for this heavenly goddess if that was what she required.
“Aunt Vanessa wants you to just relax and do your little tinkle in your diapers. Can you do that for me?”
Strangely enough, as my orgasm subsided and my tiny wee-wee began to shrink back to it’s not-so-impressive one inch size, I felt a growing need to urinate. I thought her request was a bit odd but in my state of lingering bliss, I didn’t give it a second thought. Closing my eyes, I just relaxed and let my muscles do what came naturally. In moments, the distinct sound of pee streaming into my diaper could be clearly heard.
“That’s my baby,” Vanessa coaxed me softly as she squeezed my hand. Looking up into her beautiful dark eyes, I couldn’t help but blush as the the front of my diapers became saturated and the wetness began to seep back between my legs. After about a minute, I had released everything I had been holding inside and my diapers were completely soaked. Vanessa put her hand down and felt the warm front of my panties, patting them gently.
Suddenly, her eyes focused on the wallclock and she looked back at me abruptly.
“Oh my, will you look at the time!” she exclaimed, ”your mommy will be here any minute.”
I thought I caught the faintest hint of a smile on her face and I wondered…
My mouth dropped back open and my heart began beating hard again as I realized what I had just done.
As she rose from the bed, she smoothed out the wrinkles on her short skirt and went to get a brush from her nightstand. I snapped out of my pleasant reverie and started thinking hard about what I should do about my now soaking wet diapers.
“Um, Aunt Vanessa?” I asked tentatively.
“Yes Honey?” she replied without looking away from the mirror as she brushed her luxuriant, long brown hair.
“Um…do you think you could, um, change me, before my mom shows up?” I asked hopefully.
“Hmm….” she said, taking longer to consider my question than I really thought was necessary.
Before either of us could say anything further, the doorbell rang.
Uh-oh, I thought as I felt the warm wet cloth of my diapers pressing against my skin. What was my mom going to say when she discovered them, I asked myself frantically. Why did I do it, I demanded of myself. Now I’d never get out of diapers, no matter what excuse I thought of! Except I couldn’t think of even the lamest excuse at the moment!
Vanessa left me to my panicky thoughts as she went to answer the door. Sure enough, it was my mom and Vanessa went on to explain to her that I had wanted to play dress-up with Brittany and they had found a “cute” dress for me to wear. She made it sound like it was all my idea and my mom simply shook her head at her sissyish son standing before her. I was only half listening as I was still trying to figure out how I’d explain my wet diapers to her. Wouldn’t you know it, the next thing she did was to slip one of her fingers underneath the legband of my plastic panties. The wetness inside was plain to see as she rubbed her fingers together in front of me.
“Soaked again,” she said, obviously fed up, “and to think I thought you’d reached the maturity level to move on to training pants,” she said shaking her head.
“Well? What have you got to say for yourself?” she demanded.
“Um, I-um, ah…I dunno,” I stammered.
My sense of well being from the orgasm evaporated like drops of water hitting a hot stove as she reached down and swatted me on the thick seat of my diapers. Her firm hand landed with a dull thud but I squealed like a little girl anyway.
“Vanessa, you were quite right. I’m going to make sure Jimmy stays in diapers from now on…day and night.”
Crossing her arms, she looked down at me, her disappointment obvious.
“Jimmy, I don’t know what’s gotten into you but you can just forget about those training pants you wanted. You’ll be in diapers for as long as you’re under my roof. Now get out to the car, you little sissy!” she punctuated her last remark with another sharp smack to my diapered bottom.
I began crying softly as we went out the door and as Vanessa said goodbye to us, it seemed to me that her smile was filled with satisfaction.

So began my long and humiliating path down the road to complete sissyhood.


The following morning, I awoke to my dismay to discover that I had soaked my diapers sometime during the night. I could feel the wetness all the way back through my seat and even around where the diapers were pinned. The cool, wet cloth clung to my clammy skin, forcing me to face my infantile lack of control. I was at a loss to understand why it had happened and I couldn’t believe that I hadn’t been awakened by the sensation. I knew my mom wouldn’t be happy about it–I just hoped and prayed I wouldn’t earn another trip over her lap. By now, there was no hope whatsoever of convincing her to let me wear training panties, never mind, my big boy underwear. That was definately a thing of the past. Part of me even considered that maybe I did need diapers and plastic pants. My control seemed to be slipping away before my very eyes.
I considered trying to change my own diapers before my mom found out but no sooner did I get out of bed and stand up when my mom barged into my bedroom.
“How’s mommy’s little baby?” she asked as she strolled through the door.
My heart skipped a beat and I instinctively jerked away when her hand went down to check my diapers.
“Jimmy! Did you wet yourself again?” she asked angrily.
“Ummm…I um,” I said as I bit my lip in angst.
Without hesitating, she simply reached down and squeezed the seat of my thoroughly soaked diapers.
“Mm-hm. Just as I suspected,” she said as she crossed her arms over her chest, “wet, as usual.”
I stared at the floor, crestfallen.
My mom sighed heavily.
“Come along Baby Boy, it’s time for your bath, then we’ll get you changed right back into your diapers” she said as she led me out of my room.
Down the hall, she took me into the bathroom where a hot bath was waiting. I couldn’t help but notice that bubbles filled the tub and I smelled the scent of baby shampoo filling the room. Pulling down my clinging plastic panties, she allowed my sopping wet diapers to fall on the bathroom floor but as I stepped out of them, she slapped my bottom sharply.
“Oh!” I squealed in surprise, sounding more girlish than ever.
My mom frowned at me and just shook her head.
Putting me into the tub, she washed me thoroughly as she would a baby, scrubbing my private regions with great familiarity which left me blushing. Afterwards, she left me to dry myself off while she went into my bedroom to prepare my diapers.
I tried to stall as long as possible but my mom wouldn’t have any of it.
“Jimmy!” she barked from the other room, “get your sissy bottom in here.”
I blushed again at that reference and walked in with the towel wrapped around my waist in a pathetic attempt at modesty. My mom simply yanked it off me and guided me down onto the stack of thick cloth diapers waiting on my changing pad. I whimpered in embarrassment as she smeared a thick layer of diaper rash creme across my bottom and then powdered me thoroughly with baby powder.
“Hopefully, these will last you until lunchtime,” she commented dryly.
After pinning me in for the day, she snaked up a pair of white nursery print plastic panties up my legs, even as I protested vehemently.
“Noo! Those are so babyish!” I cried.
“How appropriate,” she said as she tugged them up and over my big, bulging diapers with firm, sharp movements.
Sensing that I was about to offer further verbal resistance, she pre-empted my efforts by stuffing a big pacifier into my mouth.
“Ohmmph!” I squealed as I waved my hands in the air.
“You know, you’ve hardly changed from when you were two and I was putting you into your diapers,” she said as she shook her head in disappointment.
I blushed hot with shame and sucked feverishly on the rubber pacifier filling my mouth.
After powdering me between my legs, she put my socks on and tied my sneakers in place, ensuring that my sissyish plastic panties would remain in full view for the rest of the day.
“Put a t-shirt on and come and get breakfast,” she told me tersely.
I did as I was told and as I sat down, I found a baby bottle filled with warm milk on the kitchen table.
Just then, the doorbell rang and I froze in fear.
“You stay right where you are and don’t move. I’ll get it,” my mom ordered me in her usual firm voice.
I knew better than to do otherwise and I bit my lip as I stared down at the colorful nursery characters adorning my shiny plastic panties. From where I was sitting, I couldn’t see who was at the door but I heard familiar feminine voices and they were getting closer.
My mom walked around the corner with Brittany and Tammy right behind her. Despite the fact that these two had already seen me in the most humiliating attire possible, I still blushed at their witnessing me in my “natural, everyday” state, wearing diapers and babyish plastic panties.
“Mrs. Turner, we wanted to see if Jimmy could come over and play with us today,” Brittany was asking her.
Tammy came over and was staring at my fat diapers with obvious interest.
“I think that would be wonderful,” my mom said pleased, “it’s been awhile since he’s spent any time with his friends and he’s been cooped up inside for too long.”
I think my mom was partly relieved that I still had some “friends” and she was quick to encourage them, even if she wasn’t aware of their ulterior motives.
“I didn’t know you drank from a baby bottle, Jimmy,” Tammy exclaimed.
Without waiting for a response, she picked up the bottle and put it to my lips but I turned my head away, unwilling to be embarrassed any further. She was persistent however, and she kept positioning the rubber nipple in front of my lips as I turned my head from side to side. At last, she pinched my nose and when I was forced to open my mouth to take a breath, she pushed the nipple into my mouth and held the bottle in place. I blushed hot red as she smiled down at me in satisfaction.
“That’s it Jimmy, drink from your ba-ba and you’ll grow up to be big and strong,” she said in the most condescending voice possible.
My face only grew red as I sucked the warm milk from the bottle submissively while she held it in place.
“Well, it seems as if you’ll be in good hands,” my mom observed as she watched Tammy feeding me my milk like I was a baby.
Of course, she didn’t ask me how I felt about the arrangement but I knew it would probably involve further humiliation at the hands of these two tormentors.
After I had finished my milk, my mom drove us down the street to Brittany’s house where she bade us goodbye. I had never met her mom and each time someone new saw me in my diapers, it was crushingly embarassing all over again. My mom told her about my wetting episodes, making me sound like I was no better than a little toddler who refused to be potty trained.
“That’s okay,” she said as she looked down at me smiling, “I’ve changed lots of diapers in my time, one more baby won’t make a difference.”
I tried to explain that I wasn’t a baby but my mom simply put the pacifier back in my mouth and that put an end to that. After she left, the girls took me upstairs to Brittany’s bedroom which was decorated in a typically little girl fashion. I noticed the lacey fringed curtains, the four poster bed with pink and white covers and little fou-fou items strewn about the room.
They sat me down on a vanity chair and quickly stripped me of my t-shirt.
“What are you doing?!” I protested, although not enough to prevent them from getting their way.
“We’re going to dress you up like the little sissy you are,” Brittany explained firmly, “and if you try and stop us, I’ll put you over my knee and give you a spanking.”
I gulped at her threat and I knew she wasn’t kidding. Deep down, I knew it would be foolish to try and fight her and even if I did somehow succeed against the two of them, I was pretty sure her mom would paddle me for being disruptive. But I was also pretty sure that I’d never get that far with the two of them anyway. I was fairly certain that Brittany could spank me by herself, if she were angered enough. I reasoned it would be better to let them have their way and I’d deal with it as best I could, rather than risk a humiliating spanking at Brittany’s hands.
From her closet, Brittany brought out a frothy little party dress made of pink satin and white lace, supported by a fluffy, multi-layered petticoat underneath that flared out the hem of the skirt.
“Here’s your new outfit, Jimmy!” she informed me as she beamed and held it before me for my inspection. All I could do was to whimper helplessly as they lowered the girlish confection over my head and buttoned it securely in back. Standing back, Brittany crossed her arms and smiled deviously at me.
“Okay Sissy. Try and take it off,” she challenged me.
I tried deperately to reach behind me and grasp the buttons that ran up the back but they remained tantalizingly out of touch. I squirmed and grunted in helplessness as I strained to reach the elusive buttons binding me. After several frustrating moments, I finally slumped my shoulders in defeat and gave up in despair.
“Perfect!” she giggled with glee, clapping her hands together.
“Now to do something about those shoes.”
The two of them quickly removed my shoes and socks, tossing them in the corner, to be replaced with some girlish knee high stockings that looked like they went with a school uniform. These were followed by some glossy black patent leather mary janes that they quickly buckled into place. With each passing moment, I was looking more and more like an effeminate sissybaby!
Without warning, Brittany surprised me and gave me several long sprays of perfume before I could pull away.
“Stop it!” I cried, sounding more girlish than I would have preferred.
“I haven’t worn that since I was in first grade,” she told Tammy, “it’s called ‘Shirley Temple’.”
The babyish scent surrounded me, giving me a constant reminder of my status.
The girls giggled and made humiliating comments about me when all of a sudden, Brittany’s mom stuck her head in the door.
There was a split second of fear as the girls wondered whether they might have gone too far but then her mom smiled broadly, obviously approving of the way these girls were treating me.
“Why don’t you bring him down when you’re done and I’ll check his diapers for you,” she said helpfully, “I’ll just go and see if I have any big enough to fit him.”
“I’m not wet!” I pouted indignantly in frustration.
“Yes yes, Dear,” she said in a babyish voice as she came in and reached down to pat the front of my thick diapers, “but I’ll go and look, just the same.”
I blushed hotly as she left the room and the girls burst into laughter.
“Why are you doing this to me!?” I cried, nearly in tears.
Brittany crossed her little arms over her chest and faced me sternly.
“Because you’re a sissy. A panty-waist, diaper wetting, sissy baby and this is exactly what you need,” she said smugly.
I balled my hands into fists and pouted while they combed my hair and put two pink ribbons into it, adding the final flourishes to my transformation. Taking me by the hand, they led me downstairs where Brittany’s mom had a baby bottle of warm milk waiting for me.
“I thought Jimmy might be thirsty,” she said as she handed the bottle to Tammy.
Taking it eagerly, she shoved it into my mouth and held it there, forcing me to suck the warm liquid in a repeat of this morning’s performance.
“Aren’t you just the cutest thing!” Brittany’s mom exclaimed, “you look so natural in that dress and your diapers…how old did you girls say he was?”
“Almost eleven,” Tammy said as she kept the bottle jammed in my mouth.
Her mom shook her head, looking down at the biggest sissy she’d ever laid eyes on.
“He looks more like four to me,” she said, barely suppressing a giggle.
Tears of shame trickled down my cheek as I nursed from the bottle.
“I was able to find a few diapers that I think will fit him, when he wets his,” her mom added.
“Let’s just check our little baby,” she said as he reached down and slid a finger up under the legband of my plastic panties.
“Still dry,” she remarked with surprise.
I blushed again at her assumption but as I stood there in my frilly dress, diapers and mary janes, drinking milk from a baby bottle, I felt like I was sliding down the slippery slope of sissyhood, helpless to prevent my fall.
“I’ve got a little surprise for you…” Brittany’s mom said to me in a teasingly sing-song tone of voice.
I swallowed hard at the thought of further surprises.
“What is it, Mom?” her daughter asked.
“Guess who’s coming by to drop off my sewing machine?” she said, smiling openly.
Brittany’s face lit up as she understood.
“Stephanie’s mom?” she asked.
“Mmm-hmm,” she replied nodding her head, “and guess who’s coming with her?”
Brittany and Tammy clapped their hands together with joy.
“Stephanie!” they shouted.
“Mm-hmm…Jimmy, isn’t Stephie your little sweetheart at school?” she asked.
I jerked my head away from the bottle and stamped my feet in anger.
“She’s not my little sweetheart!” I denied angrily.
“But you do think she’s totally hot, don’t you Jimmy?” Tammy insisted.
I shook my head even as I blushed at their mention of her. I thought my admiration of her from afar had been a total secret but I realized now that these two obviously knew about my irrepressible crush on the pretty little brunette in my class. I had never actually verbalized my feelings toward her because I could never get up the nerve to talk to her. Nonetheless, I had long harbored secret desires for her for quite some time. Of course, I wasn’t the only one who longed for her, all the boys thought she was totally hot and I knew I didn’t stand a chance of striking up a relationship with her, never mind, making her my girlfriend.
“Well, you’ll finally get the chance to meet her. Won’t that be special?” Brittany asked me with mock sincerity.
For the first time, my predicament really struck me, and I lashed out at Brittany, slapping her hard and calling her several naughty words I had learned somewhere.
The smile immediately vanished from her mom’s face and she grasped my bare upper arm, yanking me away forcefully. With her free hand, she brought it down and smacked me on my thickly padded bottom, causing me to buck forward but without any real pain.
“Young Man! You will be very sorry you did that. And you will not use that kind of language in this house, do you understand me!?” she said angrily.
Before I could splutter out a reply, she hauled me over to the kitchen sink and started running some hot water. There was a cake of hand soap next to the sink and after lathering it up, nice and sudsy, she crammed it into my mouth, scraping off soap shavings in my mouth at the same time.
“OOOMMPHHH!!!” I squealed as I flailed my hands in the air.
“Now you just stand there and don’t even think about touching that soap unless you’d like me to send you home to your mommy with a very sore bottom,” she informed me as she shook her finger in my face.
I stood there quaking with a mixture of fear and anger as she stormed out of the room, leaving me on display for the other two. Brittany, after rubbing her arm, came over and slapped me hard, looking deep into my eyes, “now you’re really going to get it.”
Before I could think what further depridations she might be cooking up, her mom came out of the bathroom with a red rubber bag of some sort with a white tube hooked up to it.
“You’re a dirty little boy and it’s about time someone cleaned you out,” she said as she began filling the bag with hot, soapy water.
I didn’t know what she had in mind but instinctively, I knew it wouldn’t be pleasant for me.
“Come along, Jimmy,” she said, jerking me with her into the bathroom, “I’m sorry this has to be done but you’ve left me no choice.”
Setting the toilet seat down, she hung the glistening bag on the shower rail and then sat down, reaching up to the waistband of my plastic panties.
“Ooommph!!” I squealed desperately with the soap still filling my mouth and suds running down my chin. I fought to prevent her from lowering my plastic panties and we struggled, but only for a moment.
”Jimmy! We can do this the easy way…or, we can do it the hard way,” she said as she picked up a large flat hairbrush. I could easily visualize her applying it to my bottom with great enthusiasm and I quailed at the thought. I immediately stopped fighting her efforts and dropped my hands to my sides.
“That’s what I thought,” she said shaking her head as she easily lowered my panties to my knees, “just a big sissy, aren’t you?”
As if on cue, I began crying softly, overwhelmed with my experience.
“Don’t you worry little baby,” she said as she took me over her lap and began unpinning my diapers, “this will all be over soon.”
I whimpered helplessly as I felt her prodding her greased middle finger against my back hole, searching for entry. With sudden abruptness, she slipped it inside and I cried out, sounding more girlish than ever as the bar of soap slipped out of my mouth. She penetrated me deeply, and I blushed hotly at this private invasion of my bottom. In and out, her finger plunged and it stretched my tiny virgin hole to the limit. I squealed and moaned in response, kicking my feet while I tried to fathom her purpose. At last, she removed her slippery finger and I felt it being replaced by something hard and long.
“Ohhhh!” I moaned, feeling the plastic invader plunging deep into me. All of a sudden, I felt the rush of hot water flowing uninterrupted into my bowels.
I squeezed my cheeks togther but it did no good. I felt myself rapidly filling up and I gasped from the pressure.
“Mommy!” I moaned weakly.
“This is just what you need,” she said as she kept up the flow, “it’s guaranteed to clean out all those dirty words you’ve got inside you.”
I felt a bead of sweat trickle down my forehead as the pressure built stronger and stronger until finally I heard her clipping something shut.
“There,” she said as she stroked my exposed cheeks with her hand. The nozzle remained buried deep in my rump but she rubbed my bottom with a soothing motion, trying to keep me calm.
“I want my mommy,” I whined weakly but she merely ignored me and re-started the flow.
I moaned deeply and struggled to keep my place as the cramps hit me in earnest.
“I can’t take anymore!” I wailed piteously.
“Shusshh,” she said as she squeezed each cheek, “this is just what little babies like you need.”
Tears trickled down my face as I pondered the truth of that and I strained to take in the flood invading my rear end against my will. It seemed like it went on forever and ever but at long last, I finally heard the sound of the last bubbles disappearing into my rectum.
“Ah-am I d-done?” I inquired weakly.
“Not just yet,” she replied sweetly as she removed the slippery nozzle buried inside me. Picking up the hairbrush, she positioned it over my quivering fanny, which lay defenseless and inviting before her.
“I do not tolerate brawling in my house,” she said.
With that, she brought the wooden hairbrush down on my bottom with four, fiercely stinging swats, giving me a good taste of her tennis arm. Already in tears, I bawled openly as she stood me up and dumped me back down on the toilet after lifting up the seat.
“You can do your business but I want this door to remain open, is that understood?”
I nodded as I sobbed and held my head in my hands.
Brittany and Tammy watched as my bowels began helplessly emptying themselves without regard to my pride. After a few moments, they shook their heads and walked off, apparently having seen enough.

Two flushes and twenty minutes later, I stumbled out of the bathroom, my nursery print plastic panties still tangled around my calves. I hastily pulled them up as Brittany and her mom came down the hall.
“It’s diaper time, Jimmy!” the latter told me cheerily.
Once again defeated by superior females, I trudged into her mom’s bedroom where a fresh stack of diapers was waiting for me on the bed.
“Sorry I don’t have any diaper rash creme, Jimmy,” her mom told me as she pulled my panties back down and situated me on the soft layers of cloth.
“Oh my,” she said, clearly surprised as she pinched the tiny head of my penis between her fingers, “I don’t think I’ve ever seen one as small as this.”
The other girls giggled and I looked away to hide my blushing cheeks.
I said nothing as she powdered me all over and then pulled the triple stack of diapers up, to be subsequently pinned around my waist.
“Stand up,” she instructed me, holding my plastic panties in place around my knees, “and hold up the hem of your dress and petticoats.”
I slid off the bed to put my feet on the floor which had the effect of pulling the panties up and over my diapers. Her mom had to work with them a bit and I humiliatingly held my dress up out of the way but soon the fat diaper was all contained again, bulging around me in contrast to my skinny legs.
“Such a big baby,” she remarked as she looked down at me, causing me to blush anew.
As if on cue, Tammy produced the baby bottle from before, once more filled to the top with warm milk. I don’t know if it was the combination of wearing diapers constantly and being treated like a baby, or if it was my intimidation by her, but this time, I didn’t struggle as she eased the rubber nipple between my lips. It also washed away the flavor of the soap that still coated the inside of my mouth which wasn’t so bad.
Even though I was cooperating with Tammy now, she still wouldn’t allow me to hold the bottle and everytime I showed signs of slowing down, she’d tip up the end of the bottle further, forcing me to take more.
“Up, up…that’s it Baby…come on…up, up, up…drink your milk, baby, num, num,” she coaxed me.
Her mom had walked out and I had almost forgotten about her as I struggled to keep up with Tammy’s feeding. She sat me on the bed and stood over me, while Brittany watched me in silence.
“Let’s go out and play,” she said impulsively.
“Okay!” Tammy agreed.
”We can go into my backyard, I’ve got a hopscotch game set-up,” she told us.
“Uh-uh,” I said in disagreement.
I might let her get away with treating me like a baby inside but this was where I had to put my foot down. No way was she going to parade me outside where everyone would be able to see me in my sissy outfit.
“Jimmy. Maybe you’ve forgotten that I am the one who controls the hairbrush here,” she said menacingly.
I froze where I was in fear. Looking to Tammy, I saw she would be only to happy to assist Brittany in putting me over her friend’s lap for a spanking. Without waiting any further, she walked over to her vanity and picked up her hairbrush. It was oval shaped and pink but it had a flat back to it and I knew it would sting unmercifully.
“Okay!” I said terrified, jumping up in a panic.
As I walked past her, she swung the hairbrush and landed it against my bottom, making me cry out again like a little girl.
“Oh!” I exclaimed as I grabbed my well padded fanny.
The girls giggled and Brittany threw the hairbrush on the bed.
“I don’t think I’ll be needing that,” she laughed.
We went downstairs and out into the backyard, although not without a little coaxing on my part. It was a sunny day and on the cement portion of their back patio, a hopscotch pattern had been drawn out in chalk. The girls whispered amongst each other and giggled some more and I was certain they were making more plans for me. Tammy had me begin playing and I found it very humiliating, hopping and skipping like a little girl while my frilly dress lifted up each time, exposing my diapers and plastic panties to anyone within sight. I had just finished a few hops when I saw Tammy giggling and looking past me. Following her gaze, I saw Brittany filming me with her mom’s handheld video cam.
“Stop it!” I wailed, flailing my hands up in protest.
Brittany started laughing so hard at my spectacle that she couldn’t hold the camera steady.
“Here,” Tammy said, getting Brittany’s attention again, “I’ll just check to see if our baby wet her diapers.”
As Brittany zoomed in with the camera, Tammy reached over and after lifting the hem of my dress up, she squeezed the plastic covered seat of my diapers.
“Stop it!” I repeated, getting no better result than the first time I said it.
It was then that I caught additional movement out of the corner of my eye.
The backyard was fenced on two of its three sides but the back was open to a street, albeit one rarely used. However, at that particular moment, I looked over, only to discover one of the teachers from our school, staring at me from the sidewalk.
Ms. Walker was the physical fitness instructor there and quite a knockout. I guessed she was about 25 years old, rather tall, with long straight blond hair that was presently tied into a pony tail. She appeared to be jogging because she was wearing running shoes and a very, very short pair of shorts that showed off her long sexy legs. It was equally impossible not to notice the small white crop top she had on, that displayed her firm, flat tummy and round, curvaceous breasts. She was breathing a little heavy from her jog but she stared at me trying to see if it was really me.
“Jimmy?” she asked with a growing smile, “is that you?”
I blushed all over as I tried to think of something to say but I couldn’t think of anything.
“I didn’t know you still wore diapers,” she said as she turned to face me and placed her hands on her hips.
Ms. Walker was, by any standards, quite beautiful, and she knew it. Whenever she did anything, it was as if she were posing for a magazine shoot and now was no different. She thrust her perfect, bountiful chest out proudly and it was easy to see why all the male teachers lusted after her.
“My my, what a cute little outfit you’re wearing, Jimmy,” she remarked as she looked me up and down.
My face only grew redder and it was impossible to hold eye contact with this intimidating beauty but as I sneaked a glimpse up at her where she stood towering over me, I saw her breasts rising and falling within her tight top.
“Please don’t tell anyone, Ms. Walker,” I begged her in a small voice. I was worried because I was afraid she wouldn’t feel any obligation to me since we didn’t know each other at all.
She just giggled and reached down to pat me on the seat of my diapers.
“Don’t you worry your pretty little head, Sissy,” she said to me like she would a child, “it’ll be our wittle secret.”
Somehow, I didn’t believe her but she merely giggled and then turned around to jog off.
I stamped my feet in frustration even as I watched her shapely buns retreating down the lane away from me. I was being exposed to more and more people and fretted that before long, everyone would know about my diapers and sissy clothes.
“Okay, let’s play on the swing now,” Brittany said playfully.
I hadn’t swung on a swing for years and I felt childish doing it now. I was about to protest, however, a hard, piercing look from Brittany sent me waddling to the swing set before she got any angrier.
I had some difficulty getting my thick seat to fit into the strap of the swing and I found that when I finally got situated, the chains forced my dress to ride high over my waist, leaving my bulging diapers exposed in the front, and probably in back too. Tammy got behind me and started swinging me forward with strong pushes. It wasn’t long before I got some momentum, helped along by her aggressive pushing, and I was soon swinging high into the sky. I started getting scared because I felt like I wasn’t in control and I asked her to stop.
“Tammmmy!!” I wailed, “Stoooppp!”
I started getting panicky and I kicked my legs and mary janes to try and slow myself down. She responded by pushing me even harder back into the air and I squealed in terror each time I came falling earthwards. My dress blew up and over my chest as I came downwards, revealing my shiney nursery print plastic panties to the whole neighborhood. I was going too fast to jump out and I was too scared to try anyways. In my state of terror, my bladder decided to release all that pent up milk and several strong streams of pee emptied into my diapers while I swung out of control. I burst into tears and cried for her to let me down.
Apparently, my screaming like a little girl had carried into the house because the door opened and Brittany’s mom came out to investigate.
It was only when the swing slowed to a halt and my mary janes dragged in the gravel that I saw behind her, framed in the back door, Stephanie and her mother. OH NO!!!
I froze in panic even as I let go with a third and forth stream of hot pee into my waiting diapers. I tried to stiffle my tears in a frantic attempt to be manly but everything was happening too fast. Before me was the love of my life that I’d never had the nerve to speak to and here I was, sitting in front of her on a swing, with my sissy dress pulled up against my chest, revealing the diapers I had just soaked completely.
Her mouth hung open for the briefest of moments and then she abruptly broke into gales of laughter. My face turned three shades of red as I clung to the swing’s chains in a panic, my eyes darting around trying to find an escape. I was so preoccupied with the disaster that had befallen me that I ignored the sensations below as my bladder decided to empty itself in front of her. When I felt the wetness starting to seep down and between my legs, I realized what had happened and I let out a little cry of anguish. With my dress still pulled up from my diapers leaving them in full view, I hastily yanked the first thing I could grab, my see through petticoats, down to try and cover my shameful nursery print panties.
“Oh no, Jimmy,” Stephanie said between bouts of laughter, “don’t hide your pretty panties.”
Everyone else joined her in laughing and she stepped over to pull my petticoat back up and out of the way.
In the presence of the schoolmate that I idolized, I should have ripped the dress off myself right then and there but instead, I just started to cry like a baby.
Brittany’s mom simply shook her head and then turned to Tammy.
“Tam, can you go inside and look in the microwave, I think there’s another baby bottle of milk for Jimmy.”
“Sure thing,” she said, disappearing inside.
Stephanie had finally stopped laughing and she looked down at me, both literally and figuratively, as she stared at me.
“Wow, I mean…I always knew you were a sissy but…” she said shaking her head.
I was crushed. All this time I had been striving to make a good impression on her and in reality, she’d seen right through me, thinking of me as nothing more than big sissy.
“I didn’t realize you wore diapers,” she finished.
I wanted to say something about how I didn’t really require them but the wetness contained wthin my waterproof panties denied that possibility.
“I just started,” I mumbled, instantly regretting that choice of words.
“Aww, poor little baby. Are you having trouble keeping your pants dry? Is that it?” she said condescendingly.
“No!” I replied hotly, “I just–”
I didn’t know how to finish the sentance.
“I know, it’s because your mommy knows you’re a sissy,” she said full of self assurance, “just like the whole school.”
In a sudden fit of anger, I stood up out of the swing and stamped my feet on the ground.
“I am not a sissy!” I vented as I shook my fists.
Unfortunately, now that I was standing up again, the short hem of my dress rose up leaving my diapers and plastic panties now once again, fully exposed for everyone to see. Stephanie’s mom, who had been watching in silence, was now staring at the obvious wet spot in the front of my diapers, and as I followed her gaze, my face turned reddish-purple.
“I think this sissy needs his diapers changed,” she commented dryly as everyone else looked where she was looking.
I dropped my hands down in a vain attempt to cover the darkened area of wetness but the damage had already been done and more laughter followed.
“Have you already wet youself?” Brittany asked in amazement.
My lower lip started to quiver and I felt tears starting to brim in my eyes again.
Without waiting for a response, Brittany came over and squeezed the seat of my diapers, confirming everyone’s suspicions.
“Yep, he wet his diapers again, Mom.”
Stephanie gave me a look I’ll never forget for as long as I live. It was obvious to her that I was the biggest sissy in the world and that I’d be lost without my diapers.
Brittany’s mom sighed audibly.
“Well come on, Jimmy, let’s get you inside so we can change your pampers.”
The entire entourage followed us inside as I waddled miserably back to her bedroom. Apparently, she had already predicted I wouldn’t last the morning because another set of diapers were already laid out on the bed waiting for me.
I stood in place as her mom began tugging my clinging nursery print panties off my wet diaper and down my girlish legs.
“Does everyone have to be here?” I whined to her as she dabbed the wetness out of the inside of the panties at my ankles. My diaper hung about my hips heavily and the smell of pee filled the room.
“Hold your dress up Jimmy, I don’t want it to get stained,” she told me tersely, completely ignoring my question.
Stephanie continued to stare at me and I kept my head hung low in shame while I held the hem of the dress and petticoats up and away from my drooping diaper.
“I’m afraid I don’t have any plastic panties big enough to fit you so you’ll just have to wear these again Jimmy,” her mom informed me. She sounded more disgusted than sorry and I bit my lip with embarrasment.
She proceeded to unpin my wet diapers and they fell on the floor with a plop. Stephanie burst into laughter when she caught sight of the little nub of my penis. In fact, it was so small, that it stuck out from my body like a tiny protrusion, instead of hanging down as it would on most males. As she held a hand over her mouth and pointed with the other one, I attempted to hide the pathetic organ but Brittany’s mom slapped my hands away while she busied herself wiping my groin area with a baby wipe. Yanking me around to face the bed, she continued her ministrations, wiping my dampened cheeks and especially around my little hole, showing absolutely no respect for my dignity, such as it was.
With a harsh slap delivered to my bottom, she ordered me to get on the bed.
I let out a yelp and turned around, sitting myself on the thick rectangle of soft cloth diapers that she’d arranged.
At that moment, Tammy came over and without asking, pushed the baby bottle nipple before my lips. I didn’t want to nurse on it, particularly now that Stephanie was watching me and I pulled my head away. She merely followed my movements and persisted on pushing the nipple against my lips until I meakly submitted.
Brittany’s mom continued with my diapering as she powdered me generously, causing a cloud of softly scented baby powder to fill the air around me.
“I can’t believe what a baby you are,” Stephanie commented as she looked down at me nursing from my bottle and my diapers were being pulled up.
I looked away as a tear trickled down my cheek and I sadly swallowed another mouthful of warm milk.
Brittany’s mom pinned me up nice and snugly and then began snaking my plastic panties back up my legs.
“May I?” Stephanie asked as she bent down next to her.
“Be my guest,” her mom said gladly, “I’ve already changed him once today.”
“I’m going to remember this for a long time, Jimmy,” Stephanie remarked as she slowly pulled my plastic panties up my legs, “how when you were in fifth grade and I helped change your wet diapers.”
I sucked feverishly on my bottle as I lifted my hips up while Stephanie worked my plastic panties around the bulk of my diapers. I was so humiliated, I couldn’t look at anyone in the room.
“I can see why you need to wear such thick diapers,” she remarked disparagingly, “you’re obviously a heavy wetter.”
“And frequent, from what we’ve seen,” Brittany’s mom added.
“There,” she said as she snapped back the elastic waistband of my vinyl panties against my skin, “you’re all set, Sissy. Try to keep your diapers dry and make your mommy proud, okay?”
I whimpered in embarassment as Stephanie stood up, obviously finished with me, in every sense.
“Ready to go, Mom?” she asked.
“Sure Honey, I guess we’ve seen enough here,” her mom replied.
“I know I have,” she said with a chuckle.
The two left the room without a further word to me, as I finished the bottle Tammy was holding to my lips. I sniffed in bitter resignation as I watched the girl of my dreams walk out of the room and my life forever. I knew that to her, I’d never be anything but a diaper wetting sissy, not worth a second thought, except maybe to laugh at whenever she saw me.
Brittany’s mom had been searching through her drawers and at last she turned around to face us. In her hands were a silky pair of pink panties, their seat and legs openings covered with frilly ruffles.
“I didn’t know I still had these but maybe they’ll brighten up your day,” she said as she came over to put them on me.
I looked at them aghast, and shook my head determinedly.
“I don’t wanna to wear those!” I cried, putting my hands in front of me to hold her back.
“Nonsense, Silly,” she said as she began gathering the leg holes together, “all prissy babies like their ruffled rhumba panties. You’ll feel much better when you’ve got them on.”
“Nooo!” I wailed but her mom ignored me as she worked them over my mary janes and began pulling them up my skinny legs. They looked like they were made for a baby with the three rows of white ruffles crossing the top of the seat but since I doubted they’d be able to fit me, I didn’t struggle as much as I might have. However, to my horror, her mom continued to slip them up and over my big thick diapers like they had been made for me.
I gasped in shock as she smiled down at me, obviously pleased with their fit and look.
“There you are,” she beamed at me, “now don’t those just look darling on you.”
“I don’t wanna wear them,” I whined again but she only patted the thick padding of the front of my diapers.
“Oh yes, those are there to stay,” she assured me.
Standing back up, she checked her watch and frowned.
“Hey girls,” she said to the other two, “I’ve got to run down to Mrs. Johnson’s to get some flour. Will you guys be okay while I’m gone?”
“Oh sure,” they told her, “no problem at all.”
“Okay great, I’ll be back before long, you girls be good.”
“We will, Mom,” Brittany told her.
Somehow, I didn’t share her mom’s confidence in that happening.
When she had left the house, Brittany yanked me up off the bed roughly.
“Come on Sissy, time to go back outside.”
I resisted weakly but allowed them to lead me along until I realized we were headed toward the front door.
“Nooo!” I wailed frantically.
“Come on, Sissy! You’re going to go outside whether you like it or not!” she growled at me.
I started crying right there and Brittany dropped my hand to go down the hallway, leaving me there by the front door with Tammy. For a brief moment, I thought I might have succeeded in preventing them until I saw Brittany emerge from the bathroom with her mom’s wooden hairbrush.
“Okay Sissy-boy, looks like you’re going to get that spanking after all,” she said as she grabbed me by the wrist and started taking me into the living room.
“Noo-no!” I cried, “please, please don’t spank me.”
I knew I sounded weak and pathetic but I was desperate.
She ignored me and took a seat on the couch while Tammy grabbed me from behind to prevent my escape.
“Please Brittany! Please don’t spank me-I-I-promise to-to go outside,” I sobbed.
She looked at me hard as she held the hairbrush threateningly.
“Please? I promise I’ll go,” I pleaded, sensing I might yet still be able to escape my punishment.
“Okay…” she said grudgingly, “but you’d better get out there right now. And don’t wait for us.”
I skirted around Tammy who was also glaring at me and went to the front door. With heavy trepidation, I cracked open the door and peeked outside. No one was in sight except for the mailwoman’s vehicle, parked across the street, and I eased myself outside like I was slipping into a pool of cold water. I felt a rude push from behind me as Tammy shoved me out onto the lawn where anyone could easily see me. Behind her, Brittany came outside and was turning around with her back to me. My heart sank as I heard her locking the front door, effectively cutting off any chance of escape I might have harbored.
Suddenly a gust of wind came up and it blew the back of my dress and petticoats up and over my back.
I squealed with embarrassment as I fought to hold them down and keep my panties at least somewhat covered.
“Well, well,” I heard the mail woman say from behind me, “looks like someone’s been playing in mommy’s closet.”
I blushed hot red as I turned to see her standing and appraising me, a collection of mail in her hands.
Generally speaking, the uniforms for the U.S. postal service aren’t very sexy, nor are they particularly flattering to a woman’s figure however, this mail lady was certainly filling hers out nicely.
I gaped as I faced her, noting that her shirt was stretched to the limit trying to contain her immense breasts inside. There were even gaps between the buttons and it looked as though they were ready to pop off at any moment if she were to take a deep breath. Her shorts showed that she had smooth, tanned legs, accustomed to regular exercise.
“Here you are little boy,” she said as she handed me their mail, “or should I say baby girl?”
I felt the blood rush from my face all the way to my ears but I said nothing as she smirked at me and then turned away to continue her route.
Just when I thought things couldn’t get any worse, I saw my mom’s familiar car coming down the street. Oh no!
My mind raced as I sought desperately for a plan. She would not be happy to see me dressed like this and my mind went blank as I struggled to come up with an excuse, any excuse as to why I was wearing a frilly dress and rhumba panties out in public.
I started running for the back yard but Tammy cut me off and roughly pushed me down on the grass.
“Let me go!” I whimpered, sounding just like the little girl I was dressed up as.
My mom’s car pulled into the driveway and I saw her distinctly, staring hard at me through the side window and clearly angry with what she saw. I stood up on wobbly legs, realizing belatedly that it was too late run and hide.
My mom slammed the door of her car forcefully and strode over to where we were gathered.
“Jimmy. You have got five minutes to explain why you’re dressed up like that,” she barked at me.
My heart was beating wildly now, fearful of my mom’s wrath and my mouth went suddenly dry.
“I-I…they made me!” I shouted compulsively, pointing at the other two girls in the vain hope I could somehow make my charge stick.
My mom’s brow creased skeptically.
“They made you?” she said doubtfully.
“Uh-huh. They ganged up on me and made me dress up like this,” I explained, hoping I could make her believe me.
My mom crossed her arms and faced the other two who had so far, remained silent.
“Is that true, Brittany?” she asked, her face set in an intimidating grimace.
“No Ma’am,” she replied very innocently, “Jimmy wanted to try on some of my stuff, that’s all.”
“Nuh-uh!” I stammered, seeing my story already beginning to fall apart, “they made me!”
“You mean to tell me that these two girls, who are both smaller than you, made you dress up like this?” she said as she waved her hand disgustedly at my outfit.
“Uh-huh,” I mumbled, deeply ashamed at the admission.
My mom stared down at me, her eyes drilling into my head, which by the way, still contained the pink barettes.
Turning back to Brittany, she regarded her severely.
“Young Lady, now I want the truth here,” my mom demanded angrily.
“Jimmy said he wanted to play dress up–honest, Mrs. Turner!” she insisted urgently, “he asked us if we would dress him up like a girl so he could be like one of us.”
My face went red with rage.
“That’s a lie!!” I cried out vehemently.
My mom’s hand swooped down and smacked my pantied bottom forcefully.
“That’s enough out of you!” she barked, “are you telling me that Jimmy asked you to dress him up like this?”
“Yes Ma’am,” Brittany said sincerely.
My eyes were like knives as I glared at her, seething.
“Well I think I’ve heard enough,” my mom said as she reached into her purse and produced the paddle from home, “Jimmy, I’ve had it up to here with your sissyish behaviour.”
“But–” I tried.
“-Don’t interrupt me when I’m talking to you. I am going to spank the sissy out you if I have to put you over my knee every day.”
With that she yanked me over to the picnic bench in their yard and sat down, pulling me next to her.
“But she made me wear this stuff,” I wept bitterly.
As my mom began tugging my ruffled rhumba panties down off my diaper, I tried desperatly to stop her. It was ironic that I had fought to keep from having to wear these sissyish underwear but now they were the first thin line of defense to keep my bottom from being bared for a spanking. As I reached down to stop my mom, she slapped my hands sharply and I jerked them away. Like many a naughty girl before me, my lacey panties went down my legs to gather around my ankles.
“I don’t believe you, Jimmy. And you’d better start telling the truth because we’ll get to the bottom of this shortly. That I can assure you.”
I stamped my feet in frustration while the girls watched me with avid interest as I was about to recieve my punishment.
“Please Mommy. Please don’t spank me!” I sobbed as tears started to trickle down my face. It seemed like I had been trying to avoid getting spanked all day and now it was finally going to happen.
My mom ignored me as she yanked my nursery print plastic panties down to my knees and pulled me over her lap. Looking up, I saw Brittany and Tammy smiling broadly at my predicament and intuitively, I knew I’d never get even with them. They would always have the upper hand on me no matter what.
My mom wasted no time in unpinning my diapers and pushing them back between my legs while she tossed forward the frilly hems of my petticoats and party dress, exposing my naked fanny for everyone to see.
“Please Mommy, please!” I begged piteously but I knew it was in vain.
With a crisp SMACK!!, her paddle slapped my round, youthful cheeks causing me to cry out loudly.
“OOWWW!!” I wailed helplessly.
That paddle stung like nobody’s business and I kicked my feet deperately in response as I burst into an infantile display in front of everyone.
I bawled like a baby, beating my fists on the ground as my mom spanked away at my defenseless fanny. As I kicked and squirmed, my ruffled and plastic panties restricted my legs.
The last slap of her paddle hit my bottom right in the center, in the plump, round region of my fanny which by now, must have turned a very bright shade of red.
I wailed out as the tears streamed down my face without end and my breath came in ragged sobs.
After tanning my rump to a nice even, cherry red, she stopped for a moment, holding the paddle suspended over it.
“Now. You are going to tell me what happened here and you’d better tell the truth,” she said harshly.
As I lay there crying, I debated what was the best course of action for me to take. Obviously, she was refusing to believe that I had been overcome by two small girls so that only left one alternative…
I howled out in pain since I apparently was taking too long.
“I-I-I asked them…” I sobbed between gasps for breath.
“You asked them what,” my mom demanded.
“I-I-I asked them if I could, uh, kinda dress up,” I stammered uncertainly.
The girls held their hands over their mouths as they stiffled a giggle and my face burned with shame.
“So you asked them to dress you up like a little baby girl?” my mom asked insistently, if not doubtfully.
“Y-yes, M-Mommy,” I said uncertainly, both sets of cheeks, now a deep shade of red. I prayed my admission would earn me a reprieve from the painful and humiliating spanking.
“Jimmy. I am extremely disappointed in you. Here I thought I was raising a young man but I come to find that you’re nothing but a diaper wetting sissy. What do you have to say for yourself?” she scolded me.
I didn’t have any idea what to say or how I could avoid further punishment.
“Very well. If you’re going to act like a sissy, I’m going to treat you like one.”
With that, she brought the paddle down again and again, re-igniting the inferno on my bottom. I kicked and flailed as my mom spanked away at my behind, leaving it stinging and burning. The girls watched as I was reduced to a blubbering sissy crybaby, who very much needed his diapers.
I kicked and kicked, as the paddle slapped away at my helpless fanny and I cried unashamedly.
At last my mom finished, having released most of her frustration in the effort. I lay in place, sobbing uncontrollably as she repinned my diapers back in place. Helping me up on my shakey legs, I stood weakly holding my dress up while she tugged my plastic panties back up and over my diapers. She struggled impatiently as she wrestled them over the bulky cloth and the others watched me with smiles on their faces as I sobbed miserably.
“I had hoped that putting you back into diapers would have discouraged your infantile behaviour but I can see now that I was wrong,” she scolded me as she reached down and started pulling up my frilly rhumba panties, “since you want to dress up like a little girl so badly, fine.”
I shook my head in protest even as I sobbed in front of her like a baby.
“You can just wear your little outfit home and the rest of the day,” she said angrily, “and maybe I can look around and see if there’s some more girly clothes we can find to dress you up in.”
“But I don’t wanna wear-” I blurted out but my mom jerked me around and abruptly swatted the seat of my diapers.
“I don’t want to hear another word out of you, do you understand me?” she said as she shook her finger in my face.
I nodded tearfully and allowed her to finish pulling my rhumba panties up and over my bulging diapers.
“I’m sorry if we caused any problems,” Brittany said with a show of acted concern.
“It’s not your fault Brittany. It’s my sissy son, who can’t seem to grow past the age of two,” she replied in disgust. She dug in her purse and produced a large pacifier, which she pushed into my quivering mouth, effectively stiffling my whimpers.
“Come along Jimmy,” she said as she yanked me out to the car by my wrist.
“Bye Jimmy!” the girls said happily and in unison.
I looked over my head to see Brittany, the architect of my humiliation wink and blow a kiss at me.
“I hope you can come back over soon!” she called out.
I sucked my pacifier and prayed that wouldn’t happen anytime soon.